Herbicidal sulfonamides

ABSTRACT

Novel compounds of Formula I are useful as herbicides and plant growth regulants.

RELATED APPLICATION

This is a continuation-in-part of application U.S. Ser. No. 743,955 filed June 12, 1985, now abandoned.

BACKGROUND OF THE INVENTION

No. EP-A-44,209 discloses herbicidal sulfonamides of formula ##STR1## wherein R is H, F, Cl, Br, NO₂, CF₃, C₁ -C₃ alkyl or C₁ -C₃ alkoxy;

R₁ is H, Cl or C₁ -C₄ alkyl;

R₂ is H or CH₃ ; and

L is, among other values, CO₂ R₁₀, CONR₃ R₄, CN, Cl, Br, NR₃ R₄, S(O)_(n) R₇, SO₂ NR₃ R₄ and OR₉.

No. EP-A-112,803 discloses, in part, herbicidal sulfonamides of formula ##STR2##

South African Patent Application No. 84/2722 discloses herbicidal sulfonamides of formula ##STR3## wherein A is CR₆ R₇ XR₈, CR₉ R₁₀ R₁₁ or CHR₇ SCQR₂₁ ;

R₉ and R₁₀ are, among other values, H or CH₃ ; and

R₁₁ is COR₂₄ or a C₁ -C₄ alkyl group substituted with, among other values, CN, NO₂, OH, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkoxy, NR₁₂ R₁₃ and SO₂ NR₁₅ R₁₆.

No. EP-A-162,723 discloses 2,5-substituted herbicidal sulfonamides of formula ##STR4## wherein R is H or CH;

R₁ is C₁ -C₃ alkyl; and

R₂ is C₂ -C₆ alkoxy, C₁ -C₆ alkylthio, C₃ -C₆ alkenyl, C₃ -C₆ alkynyloxy, C₃ -C₆ alkenylthio, C₃ -C₆ alkynylthio, OCH₂ CH₂ OCH₃, OCH₂ CH₂ SCH₃, CH₂ F, CHF₂, OCF₂ H, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, OCH₂ CH₂ Cl, C₂ -C₆ alkyl substituted with 1-3 atoms of F or Cl or C₁ -C₄ alkyl substituted with C₁ -C₂ alkoxy or C₁ -C₂ alkylthio.

SUMMARY OF THE INVENTION

This application pertains to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants. ##STR5## wherein E is CH₂ or a single bond;

W is O or S;

R is H or CH₃ ;

R₁ is F, Cl, Br, NO₂, C₁ -C₄ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, OCH₂ CH₂ OCH₃, C₁ -C₄ haloalkoxy, C₃ -C₄ alkenyloxy, C₂ -C₄ haloalkenyloxy, C₃ -C₄ alkynyloxy, CO₂ R₃, CONR₄ R₅, SO₂ NR₄ R₅, SO₂ N(OCH₃)CH₃, S(O)_(n) R₆, OSO₂ R₇, C₁ -C₂ alkyl substituted with C₁ -C₂ alkoxy, OH or C₁ -C₂ alkylthio, CH₂ CN, C₆ H₅, ##STR6## R₂ is ##STR7## R₃ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, ##STR8## CH₂ CH₂ Cl, CH₂ CH₂ F, or C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ ;

R₄ is C₁ -C₃ alkyl;

R₅ is H or C₁ -C₃ alkyl;

R₄ and R₅ may be taken together to form (CH₂)₃ or (CH₂)₄ ;

R₆ is C₁ -C₃ alkyl, CH₂ CH═CH₂ or CH₂ C.tbd.CH;

R₇ is C₁ -C₃ alkyl or N(CH₃)₂ ;

R₈ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CH₂ CH₂ Cl, CH₂ CH₂ F, C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ or C₃ -C₆ cycloalkyl;

R₉ is C₁ -C₂ alkyl;

R₁₀ and R₁₁ are independently C₁ -C₂ alkyl, C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, NHCH₃ or N(CH₃)₂ ;

R₁₂ and R₁₃ are independently H or C₁ -C₂ alkyl;

R₁₄ is C₁ -C₃ alkyl;

R₁₅ is H or CH₃ ;

R₁₆ is H, C₁ -C₂ alkyl or F;

R₁₇ is H or C₁ -C₂ alkyl;

R₁₈ is C₁ -C₂ alkyl;

R₁₉ is H, Si(CH₃)₃ or C₁ -C₂ alkyl;

R₂₀ is H or C₁ -C₂ alkyl;

p is 1 or 2;

n is 0, 1, or 2;

A is ##STR9## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, halogen, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino or di(C₁ -C₃ alkyl)amino;

Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylthioalkyl, C₂ -C₅ alkylsulfinylalkyl, C₂ -C₅ alkylsulfonylalkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkynyl, C₃ -C₅ cycloalkyl, azido, cyano, ##STR10##

m is 2 or 3;

Q₁ and Q₂ are independently O or S;

R_(a) is H or C₁ -C₃ alkyl;

R_(b) and R_(c) are independently C₁ -C₃ alkyl;

Z is CH, N, CCH₃, CC₂ H₅, CCl or CBr;

Y₁ is O or CH₂ ;

X₁ is CH₃, OCH₃, OC₂ H₅ or OCF₂ H;

X₂ is CH₃, C₂ H₅ or CH₂ CF₃ ;

Y₂ is OCH₃, OCH₂ H₅, SCH₃, SC₂ H₅, CH₃ or CH₂ CH₃ ;

X₃ is CH₃ or OCH₃ ;

Y₃ is H or CH₃ ;

X₄ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl;

Y₄ is CH₃, OCH₃, OC₂ H₅ or Cl;

and their agriculturally suitable salts; provided that

(1) when X is halogen, then Z is CH and Y is OCH₃, OC₂ H₅, NH₂, NHCH₃, N(CH₃)₂, OCF₂ H or N(OCH₃)CH₃ ;

(2) when X or Y is C₁ haloalkoxy, then Z is CH;

(3) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, ##STR11## (4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R₁ and R₂ is less than or equal to six;

(5) when R₂ is C(O)R₁₇, then R₁ is other than C₁ -C₄ haloalkyl or C₂ alkyl substituted with C₁ -C₂ alkoxy or C₁ -C₂ alkylthio, and Y is other than cyclopropyl;

(6) when Y is C₂ -C₅ alkylthioalkyl, C₂ -C₅ alkylsulfinylalkyl or C₂ -C₅ alkylsulfonylalkyl, then R₂ is other than CH(R₁₇)NO₂ ; and

(7) X₄ and Y₄ are not simultaneously Cl.

In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.

Alkenyl denotes straight chain or branched alkenes, e.g., vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.

Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be monohalogenated or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.

The total number of carbon atoms in a substituent group is indicated by the C_(i) -C_(j) prefix where i and j are numbers from 1 to 5. For example, C₁ -C₃ alkylsulfonyl would designate methylsulfonyl through propylsulfonyl, C₂ alkoxyalkoxy would designate OCH₂ OCH₃ ; C₄ alkoxyalkoxy would designate the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of 4 carbon atoms, examples including OCH₂ OCH₂ CH₂ CH₃ and OCH₂ CH₂ OCH₂ CH₃ ; as a further example, C₂ cyanoalkyl would designate CH₂ CN and C₃ cyanoalkyl would designate CH₂ CH₂ CN and CH(CN)CH₃.

Preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are:

1. Compounds of Formula I where

W is O; and

R is H;

2. Compounds of Preferred 1 where

E is a single bond;

X is C₁ -C₂ alkyl, C₁ -C₂ alkoxy, Cl, F, Br, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; and

Y is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, CH₂ OCH₃, CH₂ OCH₂ CH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, CH₂ SCH₃, ##STR12## OCF₂ H, SCF₂ H, cyclopropyl, C.tbd.CH or C.tbd.CCH₃ ; Z is CH or N;

3. Compounds of Preferred 2 where R₂ is CH₂ CN, CH₂ N₃, ##STR13## 4. Compounds of Preferred 3 where A is A-1. 5. Compounds of Preferred 4 where R₁ is F, Cl, Br, NO₂, C₁ -C₃ alkyl, C₁ -C₂ alkyl substituted with 1-3 F or Cl or 1 Br, C₂ -C₃ alkenyl, C₂ -C₃ alkenyl substituted with 1-3 F or Cl, C₁ -C₂ alkoxy, C₁ -C₂ alkoxy substituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy, OC(Cl)═CHCl, CO₂ Ch₃, CO₂ CH₂ H₅, CO₂ CH₂ CH═CH₂, CO₂ CH₂ CH₂ CL, CO₂ CH₂ CH₂ OCH₃, CONH(C₁ -C₂ alkyl), CONCH₃ (C₁ -C₂ alkyl), SO₂ N(OCH₃)CH₃, SO₂ NH(C₁ -C₂ alkyl), SO₂ N(C₁ -C₂ alkyl)₂, S(O)_(n) C₁ -C₃ alkyl, OSO₂ Ch₁ -C₃ alkyl, C.sub. 1 -C₂ alkyl substituted with OCH₃ or SCH₃, C₆ H₅ and R₁ -A, R₁ -B, R₁ -C, R₁ -D, R₁ -E, R₁ -F, R₁ -G, R₁ -H, R₁ -I, R₁ -J, R₁ -K, R₁ -L, R₁ -M, R₁ -N, R₁ -O, R₁ -P, R₁ -Q R₁ -R, R₁ -S, R₁ -T, R₁ -U, R₁ -V or R₁ -W;

6. Compounds of Preferred 5 where

X is CH₃, OCH₃, OCH₂ CH₃, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

7. Compounds of Preferred 6 where R₁ is F, Cl, Br, NO₂, CH₃, CF₃ C₁ -C₂ alkoxy, allyloxy, OC(Cl)═CHCl, CO₂ CH₃, CO₂ C₂ H₅, CO₂ NHCH₃, CO₂ N(CH₃)₂, SO₂ NHCH₃ SO₂ N(CH₃)₂, SO₂ CH₃, SO₂ C₂ H₅, OSO₂ CH₃, OSO₂ C₂ H₅, R₁ -A, R₁ -B or R₁ -C.

Specifically preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are:

4-(cyanomethyl)-2-[[4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 177°-179° C.; and

4-(cyanomethyl)-2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 160°-163° C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The compounds of Formula I can be prepared from sulfonamides of Formula II and heterocyclic amines of Formula III by one or more methods described in the literature. ##STR14## Several representative routes are described below. U.S. Pat. No. 4,394,506 (issued 7/19/83) teaches the conversion of sulfonamides to sulfonyl isocyanates and sulfonyl isothiocyanates, and their subsequent coupling with heterocyclic amines of Formula III to give sulfonylureas.

U.S. Pat. No. 4,398,939 (issued 8/16/83) teaches the formation of n-butylsulfonylureas from sulfonamides followed by phosgenation to give the sulfonyl isocyanates. Alternatively, the sulfonamides can be treated with thionyl chloride followed by phosgenation to afford the sulfonyl isocyanates. Additionally, methylcarbamate derivatives of compounds of Formula III react with sulfonamides in the presence of trimethylaluminum to give sulfonylureas.

U.S. Pat. No. 4,443,245 (issued 4/17/84) teaches two methods for the synthesis of sulfonylureas. Either a phenyl carbamate of a sulfonamide and a heterocyclic amine, or a sulfonamide and a phenyl carbamate of a heterocyclic amine couple to give a sulfonylurea in an inert solvent with base.

The preparation of sulfonamides from sulfonyl chlorides is widely reported in the literature; for reviews see: F. Hawking and J. S. Lawrence. "The Sulfonamides," H. K. Lewis and Co., London, 1950 and E. H. Northey, "The Sulfonamides and Allied Compounds," Reinhold Publishing Corp., New York, 1948.

Additionally, primary sulfonamides, such as those of Formula II, can be formed by removal of an N-t-butyl protecting group from the corresponding secondary sulfonamide with trifluoroacetic acid (J. D. Catt and W. L. Matier, J. Org. Chem., 39, 566 (1974)) or polyphosphoric acid (J. G. Lombardino, J. Org. Chem., 36 (1971), 1843).

The requisite sulfonyl chlorides may be synthesized by known methods or with slight modifications thereof, by one skilled in the art. Several representative teachings are listed below.

Aromatic nitro groups may be transformed into sulfonyl chlorides by reduction, diazotization and coupling with sulfur dioxide/cupric chloride as taught in U.S. Pat. No. 4,310,346 (issued 1/12/82).

European Publication No. 94,821 (published 11/23/83) describes the displacement of aromatic halides with thiolate anions and subsequent oxidative chlorination to yield sulfonyl chlorides.

Halogen-metal exchange of aromatic halides or proton-metal exchange of aromatics followed by quenching with sulfur dioxide gives sulfinate salts. These salts yield sulfonyl chlorides upon reaction with N-chlorosuccinimide as taught in U.S. Pat. No. 4,481,029 (issued 11/6/84). Directed proton-metal exchange of aromatic compounds has been reviewed by Gschwend and Rodriguez, Org. Reactions, 26 (1979), 1. Directed lithiation of aryl-N-t-butylsulfonamides is described by J. G. Lombardino, J. Org. Chem., 36 (1971), 1843. Also, aryllithiums may be converted directly to arylsulfonyl chlorides with sulfuryl chloride as described in S. N. Bhattacharya, et. al., J. Chem. Soc. C, (1968), 1265.

Electrophilic chlorsulfonation of an aromatic ring to give a sulfonyl chloride is well known in the literature. This technique works best for alkyl aryl ethers and alkyl aromatics. Its application is described by E. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 511-14 and 603-4.

Transformation of phenols to sulfonyl chlorides can be accomplished by the formation of a thiocarbamate, rearrangement, hydrolysis and oxidative chlorination as described by M. S. Newman and H. A. Kames, J. Org. Chem., 31 (1966), 3980.

Compounds of Formula II can be prepared by a variety of methods known in the literature. The most universal scheme, where benzyl halides of Formula IV are reacted with the appropriate reagent, is shown below. ##STR15## wherein U is SO₂ NH₂ or a previously described sulfonamide precursor, and X¹ is Cl, Br or I and R₂ is of the structure --CH(R₁₇)--. Some specific methods are listed below.

NITRILES (R₂ ═CH(R₁₇)CN)

Nitriles can be prepared by nucleophilic displacement of benzyl halides, usually benzyl chlorides or bromides, with potassium or sodium cyanide. Many solvents are applicable, but frequently dimethylsulfoxide is used. Thus, a benzyl bromide of formula IV can be contacted with potassium cyanide in dimethylsulfoxide for 0.5 h to 24 h at 20° to 140° C. For a review of this reaction, refer to Friedrich and Wallenfels, in Rappoport, "The Chemistry of the Cyano Group", pp. 77-86, Interscience Publishers, New York, 1970.

ISONITRILES (R₂ ═CH(R₁₇)NC)

Heavy metal cyanides and benzylhalides react to give isonitriles. The reaction is best carried out in the dark using silver cyanide and a benzyl iodide. Typical procedures are given by A. Gautier, Ann. Chem., 142 (1867), 28 and H. L. Jackson and B. C. McKusick, Org. Syn., Col. Vol. IV, 438.

AZIDES (R₂ ═CH(R₁₇)N₃)

Compounds of Formula II may be prepared by reacting an azide anion with a benzyl halide. Typically sodium azide in alcohol or wet acetone is mixed with a benzyl bromide at 20°-100° C. This nucleophilic displacement is reviewed in Biffin, Miller and Paul, in Patai, "The Chemistry of the Azido Group," pp. 57-119, Interscience Pub., New York, 1971.

PHOSPHONATES (R₂ ═CH(R₁₇)P(O)R₁₀ R₁₁)

Alkyl phosphites are heated with benzylic halides to give phosphonates. The reaction is known as the Arbuzov reaction and it is reviewed by Arbuzov, Pure Appl. Chem., 9 (1964), 307-335.

AMINES (R₂ ═CH(R₁₇)NR₁₂ R₁₃)

Tertiary amines are prepared by alkylation of a secondary amine with a benzylic halide. The reaction is well documented in the literature.

Primary amines can be prepared by reduction of compounds of Formula II where R₂ is azide. Generally lithium aluminum hydride or hydrogen and palladium catalyst are used.

NITRO (R₂ ═CH(R₁₇)NO₂)

Nitrites react with benzylic halides to give benzylic nitro compounds. The reaction is usually carried out with sodium nitrite on a benzylic bromide in dimethylformamide or dimethylsulfoxide. When silver nitrite is used, diethyl ether at 0°-25° C. are the preferred reaction conditions. The reaction is exhaustively discussed by N. Kornblum, Org. Reactions, 12 (1962), 101.

SELENO ETHERS (R₂ ═CH(R₁₇)SeR₁₄)

Alkali alkylselenides can be prepared by in situ combination of an alkali metal t-butoxide with the selenol HSeR₁₄ in the solvent to be used for the displacement reaction. The selenols, HSeR₁₄, can be prepared by a variety of methods reviewed by D. L. Klayman, "Selenols and their Derivatives" in Organic Selenium Compounds: Their Chemistry and Biology, D. L. Klayman, W. H. H. Gunther ed., New York, 1973, and K. J. Irgolic and M. V. Kudchadker, "Organic Chemistry of Selenium" in Selenium, R. A. Zingaro, W. C. Cooper ed., Van Nostrand Reinhold, New York, 1974.

Benzyl halides may be formed through a variety of methods described in the literature. Several are listed below.

BENZYLIC CHLORIDES (X¹ ═Cl)

Treatment of alkyl benzene derivatives with N-chlorosuccinimide, NCS, in a suitable solvent, such as carbon tetrachloride or dichloromethane, and catalyzed by light or a free radical initiator, such as azoisobutyronitrile or benzoyl peroxide, gives the benzylic chloride.

Treatment of a benzylic alcohol with thionyl chloride, either neat or in the presence of a base such as pyridine, gives the benzylic chloride. For typical examples, see H. Gilman and J. E. Kirby, J. Am. Chem., Soc., 51, 3475 (1929) and M. S. Newman, J. Am. Chem. Soc., 62, 2295 (1940).

BENZYLIC BROMIDES (X¹ ═Br)

Treatment of alkyl benzene derivatives with N-bromosuccinimide by a method analogous to the case of N-chlorosuccinimide gives the benzylic bromide. Benzylic alcohols in an inert solvent such as benzene or dichloromethane react with phosphorus tribromide to give benzylic bromides.

BENZYLIC IODIDES (X¹ ═I)

Treatment of a benzylic chloride or benzylic bromide with sodium iodide gives the benzylic iodide. The reaction, known as the Finkelstein reaction, works well in refluxing acetone.

Benzylic alcohols may be treated with iodine and phosphorus (red) or phosphorus (red) and phosphorus (yellow) to give the benzylic iodide.

Compounds of Formua II, where R₂ contains an oxygen functionality, such as an aldehyde or ketone, may be prepared by a variety of methods known to one skilled in the art. Two such routes are shown below. ##STR16##

Primary and secondary benzylic halides may be oxidized to aldehydes and ketones, respectively using dimethylsulfoxide. For reviews of this reaction see Durst, Adv. Org. Chem., 285-388 (1969) pp. 343-356 and W. Epstein and F. Sweat, Chem. Rev., 67 (1967), 247-60.

Primary benzylic alochols may be oxidized to aldehydes and secondary benzylic alcohols may be oxidized to ketones by one skilled in the art. One or more of a variety of methods, such as an oxidizing agent, catalytic dehydrogenation, Oppenauer oxidation or halosuccinimide oxidation may be used.

Acetals, thioacetals, ketals and thioketals are easily prepared by one skilled in the art from compounds of Formula V.

Oximes, and oxime ethers of Formula Va are easily prepared by one skilled in the art from compounds of Formula V and hydroxylamine or o-alkyl-hydroxylamine with or without an appropriate base. ##STR17##

Benzylic alcohols and alkyl benzene derivatives are either known or may be prepared by one skilled in the art.

The heterocyclic amines A-1 to A-7 are either known, disclosed in this application or can be prepared by methods obvious to one skilled in the art.

For a review of the synthesis and reactions of 2-aminopyrimidines (A-1, Z═CH) see The Chemistry of Heterocyclic Compounds, Vol 16, Wiley-Interscience, New York (1962). For a review of the synthesis and reactions of 2-amino-1,3,5-triazines (A-1, Z═N) see The Chemistry of Heterocyclic Compounds, Vol. 13, Wiley-Interscience, New York (1959), F. C. Schaefer, U.S. Pat. No. 3,154,537 and F. C. Schaefer and K. R. Huffman J. Org. Chem., 28 (1963), 1812.

The synthesis of bicyclic amines A-2 and A-3 is taught in U.S. Pat. No. 4,339,267.

The synthesis of amino furo[2,3-d]pyrimidines, A-4, is taught in U.S. Pat. No. 4,487,626.

The synthesis of aminotriazoles, A-5, is taught in U.S. Pat. No. 4,421,550.

The synthesis of aminomethylheterocycles, A-6, is taught in U.S. Pat. No. 4,496,392.

The synthesis of aminocyano heterocycles, A-7, is taught in European Publication No. 125,864 (published 11/21/84).

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting copounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contacting of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water, e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is exchanged for that of the original salt of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is further illustrated by the following examples.

EXAMPLE 1 5-Bromomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide

A mixture of 27 g of N-(1,1-dimethylethyl)-2-methoxy-5-methylbenzenesulfonamide (E. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 603), 19.6 g NBS and 0.3 g azobisisobutyronitrile in 200 ml CH₂ Cl₂ was refluxed and illuminated with a sun lamp. After 8 hours the lamp was turned off and the reaction was refluxed for another 24 hr. The reaction was allowed to cool. The reaction mixture was washed with 200 ml of a 1:1:1:1 mixture of brine:sodium sulfite:sodium bicarbonate:water. The organic layer was dried (MgSO₄), treated with charcoal and filtered through a 5 g plug of silica gel. The plug was washed with 100 ml of chloroform. The combined organic fractions were evaporated to give 34 g of solid, m.p. 137°-142° C.

NMR (CDCl₃, 200 MHz)δ: 1.15 (s, CH₃, 9H), 4.0 (s, OCH₃, 3H), 4.45 (s, CH₂, 2H), 4.95 (bs, NH, 1H), 7.0-8.6 (m, ArH, 3H).

EXAMPLE 2 5-Cyanomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide

A mixture of 1.63 g potassium cyanide and 8 g of the compound from Example 1 in 50 ml of DMSO was stirred at room temperature overnight. The solution became darker in color with time, going from orange to purple to black. After being stirred overnight the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO₄), filtered and the solvent evaporated. The residual red oil was eluted through a dry silica column with 20% ethyl acetate-80% dichloromethane. The product band was isolated to give 3.0 g solid m.p. 146°-147° C.

NMR (CDCl₃, 90 MHz): 1.1 (s, CH₃, 9H), 3.7 (s, CH₂ CN, 2H), 4.0 (s, OCH₃, 3H), 5.0 (s, NH, 1H), 6.9-8.0 (m, ArH, 3H).

EXAMPLE 3 5-Cyanomethyl-2-methoxybenzenesulfonamide

A suspension of 3.0 g of the compound from Example 2 and 0.1 g p-toluenesulfonic acid in 100 ml of dry toluene was refluxed in a flask equipped with a Dean-Stark apparatus. After being refluxed overnight the solution was concentrated and allowed to cool. The precipitate was filtered off to give 0.5 g light brown solid. The mother liquor was chromatographed over silica gel with 20:73:2:5, ethyl acetate:methylene chloride:methanol:THF to give additional product, m.p. 173°-177° C.

NMR (DMSO-d₆, 90 MHz)δ: 3.9 (s, OCH₃, 3H), 4.0 (s, CH₂ CN, 2H), 7.1 (bs, NH₂, 2H), 7.2-7.8 (m, ArH, 3H).

EXAMPLE 4 5-(Cyanomethyl)-N-((4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl)-2-methoxybenzenesulfonamide

To a suspension of 0.3 g of the compound from Example 3 and 0.37 g 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 15 ml of dry acetonitrile was added 0.198 ml DBU. After being stirred overnight the clear solution was diluted with 50 ml of water, acidified with 1N HCl and the precipitate was filtered off. The residue was washed with water and triturated with ether to give 0.44 g solid, m.p. 168°-171° C. (dec.).

IR (nujol) 1711 cm⁻¹. NMR (200 MHz, DMSO-d₆)δ: 3.76 (s, OCH₃, 3H), 3.91 (s, OCH₃, 6H), 4.10 (s, CH₂, 2H) 6.02 (s, Het-H, 1H), 7.2-7.9 (m, ArH, 3H), 10.5+12.8 (S, NH, 2×1H).

EXAMPLE 5 5-(Bromomethyl)-2-carboxymethylbenzenesulfonamide

A solution of 3.5 g (0.0153 mole) of 5-methyl-2-carboxymethylbenzenesulfonamide, 2.86 g N-bromosuccinimide, 0.05 g azobisisobutyronitrile in 50 ml of carbon tetrachloride and 50 ml dichloromethane was prepared under a nitrogen atmosphere. The solution was refluxed and irradiated with a sun lamp for 4 h. Then 0.6 g N-bromosuccinimide was added. After three hours of further irradiation the reaction was cooled and filtered to give 4.7 g of a white solid. The solid was washed with 200 ml of dichloromethane to leave 1.0 g of product. The mother liquor was eluted through a dry silica gel column with 5% diethyl ether/95% dichloromethane to give an additional 2.3 g of product, m.p. 171°-173° C.

NMR (CDCl₃, 200 MHz)δ: 4.0 (s, OCH₃, 3H), 4.52 (s, CH₂ Br, 2H) 5.76 (s, NH₂, 2H), 7.6-8.2 (m, ArH, 3H).

EXAMPLE 6 5-(Cyanomethyl)-2-carboxymethylbenzenesulfonamide

To a solution of 0.31 g potassium cyanide in 20 ml of dry dimethylsulfoxide was added 1.4 g (4.55 mmol) of the compound from Example 5. After being stirred for 6 h, the reaction mixture was partitioned between ethyl acetate and water. The water layer was neutralized to pH 7, the layers separated and the organic layer was dried (MgSO₄). This solution was placed on a dry silica gel column and eluted with 40% ethyl acetate/60% hexane followed by 60% ethyl acetate/40% hexane. The product band (R_(f) 0.5, 60% ethyl acetate/40% hexane) was extracted with ethyl acetate, concentrated and the residue triturated with diethyl ether to give 0.26 g of a solid, m.p. 125°-129° C.

MS (m/e) 254 (M⁺). IR (Nujol) 1711 cm⁻¹.

NMR (200 MHz, DMSO-d₆)δ: 3.82 (s, OCH₃), 4.24 (s, CH₂ CN), 7.36 (s, NH₂), 7.65 (dd, ArH, 2H), 7.95 (s, ArH, 1H).

EXAMPLE 7 4-(Cyanomethyl)-2-[((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)aminosulfonyl]benzoic acid, methyl ester

To a suspension of 0.12 g of the compound from Example 6 and 0.143 g of 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 15 ml of dry acetonitrile was added 72.7 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After being stirred at room temperature for one hour, the reaction mixture was diluted with 50 ml of water, acidified with 1N hydrochloric acid to pH 2 and extracted with ethyl acetate. The organic solution was dried (MgSO₄), filtered and concentrated to an oil. Trituration of the residue with 3:1 (ethyl ether:acetonitrile) gave 0.16 g of a white solid, m.p. 177°-179° C.

IR (nujol) 1725 cm⁻¹.

NMR (DMSO-d₆, 200 MHz)δ: 3.78 (s, OCH₃, 3H), 3.92 (s, OCH₃, 6H), 4.31 (s, CH₂, 2H), 6.01 (S, Het-H, 1H), 7.7-8.2 (m, ArH, 3H), 10.6 and 12.7 (two s, NH, 2×1H).

EXAMPLE 8 5-Acetyl-2-ethoxybenzenesulfonamide

To a solution of 30.6 g of 4-ethoxyacetophenone in 100 ml of chloroform was added 40 ml of chlorosulfonic acid dropwise. The reaction was then reluxed for five hours after which it was poured into 800 ml of ice water. The reaction mixture was extracted with 400 ml of chloroform. The organic layer was washed with brine, dried (MgSO₄) and filtered through charcoal. The filtrate was concentrated under reduced essure to give 12.3 g of an oil. The oil was dissolved in 200 ml tetrahydrofuran. The solution was cooled to 5° C. followed by dropwise addition of 10 ml of concentrated ammonium hydroxide. After stirring overnight at room temperature, the reaction was partitioned between water and ethyl acetate. The organic layer was washed with 1N hydrochloric acid, brine, dried (MgSO₄), filtered and stripped. The residue was crystallized from acetonitrile/diethyl ether. The solid was washed with methanol and dried to give 2.3 g of solid, m.p. 148°-151° C.

NMR (90 MHz, CDCl₃)δ: 1.5 (m, CH₃, 3H), 2.55 (s, CH₃, 3H), 4.35 (q, CH₂ O, 2H), 5.1 (bs, NH₂), 7.0-8.6 (m, ArH, 3H).

EXAMPLE 9 5-Acetyl-N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2-ethoxybenzenesulfonamide

To a stirred suspension of 0.2 g of the compound from Example 8, 0.23 g of 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 10 ml of dry acetonitrile was added 127 μl of DBU. After being stirred for 1 hr, the mixture was treated with 40 ml of water and 1N HCl in a dropwise manner until the pH was 3. The precipitate was filtered off and washed with water and ether/hexane (1/1), to give 0.27 g of a solid, m.p. 192°-193° C.

IR (nujol) 1680 and 1705 cm⁻¹.

NMR (200 MHz, DMSO-d₆)δ: 1.1 (t, CH₃, 3H), 2.58 (s, CH₃, 3H), 3.91 (s, OCH₃, 6H), 4.27 (q, CH₂, 2H), 6.03 (s, Het-H, 1H), 7.2-8.4 (m, ArH, 3H), 10.6 and 12.7 (s, NH, 2×1H).

The invention is further exemplified, but not limited to the compounds in Tables I-VII. The compounds depicted in these tables may be prepared by methods described in Examples 1-9, or by modifications thereof apparent to those skilled in the art. ##STR18##

                                      TABLE I                                      __________________________________________________________________________     General Formula I                                                                                                                        m.p.                 R.sub.1     R.sub.2      W R  X           Y            Z  (°C.)         __________________________________________________________________________     F           CH.sub.2 CN  O H  OCH.sub.3   H            CH                      F           CH.sub.2 CN  O CH.sub.3                                                                          OCH.sub.3   CH.sub.3     CH                      F           CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    N                       F           CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      F           CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 CH.sub.3                                                                           CH                      F           CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    N                       F           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.2 OCH.sub.3                                                                          CH                      F           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      F           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.2 CH.sub.3                                                                         CH.sub.3     CH                      F           CH.sub.2 P(O)(CH.sub.3).sub.2                                                               O H  OCH.sub.3   CH.sub.3     N                       Cl          CH.sub.2 CN  O H  OCH.sub.3   CH.sub.2 CH.sub.2 OCH(CH.sub.3).                                               sub.2        CH                      Cl          CH.sub.2 CN  O H  Cl          OCH.sub. 3   CH                      Cl          CH.sub.2 CN  O H  OCH.sub.3   CH(CH.sub.3)(CH.sub.2 OCH.sub.3)                                               1            CH                      Cl          CH.sub.2 SCN O H  CH          CH.sub.3     CH.sub.3                                                                          143-153              Cl          CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     N  100-106              Cl          CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH 174-180              Cl          CH.sub.2 SCN O H  Cl          OCH.sub.3    CH oil                  Cl          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N  oil                  Cl          CH.sub.2 SCN O H  OCH.sub.3   (CH.sub.2).sub.4 CH.sub.2                                                      OCH.sub.2 CH.sub.3                                                                          CH                      Cl          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     N                       Cl          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCF.sub.2 H CH.sub.3     CH                      Cl          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   NH.sub.2     CH                      Cl          CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                     O H  OCH.sub.3   NHCH.sub.3   N                       Br          CH.sub.2 CN  O H  CH.sub.3    NHCH.sub.2 CH.sub.3                                                                         CH                      Br          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      Br          CH.sub.2 CN  S H  OCH.sub.3   CH.sub.3     N                       Br          CH.sub.2 SCN O H  CH.sub. 2 F OCH.sub.3    CH                      Br          CH.sub.2 SCN O H  OCH.sub.3   NHCH(CH.sub.3).sub.2                                                                        CH                      Br          CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     N                       Br          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.2 CH.sub.2 F                                                                       OCH.sub.3    CH                      Br          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   N(CH.sub.3).sub.2                                                                           CH                      Br          CH.sub.2 P(O)(SCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       NO.sub.2    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      NO.sub.2    CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      NO.sub.2    CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      NO.sub.2    CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.3     N                       NO.sub.2    CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      NO.sub.2    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.2 CH.sub.2 CH.sub.2                                                                 CH                      NO.sub.2    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       NO.sub.2    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        OCH.sub.3    CH                      NO.sub.2    CH.sub. 2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   SCH.sub.2 CH.sub.2 F                                                                        CH                      NO.sub.2    CH.sub.2 P(S)(SCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       CH.sub.3    CH.sub.2 CN  O H  CH.sub.3    SCH.sub.3    CH                      CH.sub.3    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.3    CH.sub.2 SCN O H  OCH.sub.3   SCH(CH.sub.3).sub.2                                                                         N                       CH.sub.3    CH.sub.2 SCN O H  OCH.sub.2 CH(CH.sub.3).sub.2                                                               OCH.sub.3    CH                      CH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  Br          OCH.sub.3    CH                      CH.sub.3    CH.sub.2 P(O)(N(CH.sub.3).sub.2).sub.2                                                      O H  OCH.sub.3   OCH.sub.3    N                       CH.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                           CH.sub.3    OCH.sub.3    CH                      CH.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3                                                                CH                       -n-C.sub.4 H.sub.9                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       CHCH.sub.2  CH.sub.2 CN  O H  F           OCH.sub.3    CH                      CHCHCH.sub.3                                                                               CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 CH CH.sub.2                                                                       CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    N                       CClCCl.sub.2                                                                               CH.sub.2 SCN O H  OCH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2                                                     OCH.sub.3    CH                      C CCH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      CH.sub.2 C CH                                                                              CH.sub.2 CN  O H  OCH.sub.3   CH.sub.2 CH.sub.3                                                                           N                       CH.sub.2 Cl CH.sub.2 CN  O H  N(CH.sub.2 CH.sub.3).sub.2                                                                 OCH.sub.3    CH                      CH.sub.2 Cl CH.sub.2 SCN O H  Cl          OCH.sub.3    CH                      CH.sub.2 Br CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       CH.sub.2 Br CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      CF.sub.3    CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N                       CF.sub.3    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      CF.sub.3    CH.sub.2 SCN O H  Br          OCH.sub.3    CH                      CF.sub.3    CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 CH.sub.2                                                                           N                       CF.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CF.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.2 CH.sub.3                                                                         CH.sub.3     CH                      CF.sub.3    CH.sub.2 NH.sub.2                                                                           O H  OCH.sub.3   H            CH                      CH.sub.2 CHClCH.sub.2 Cl                                                                   CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    N                       CH.sub.2 CF.sub.3                                                                          CH.sub.2 CN  O H  I           OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 CN  O H  OCH.sub.3   CH.sub.2 OCH.sub.3                                                                          CH                      OCH.sub.3   CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    N  166-170°                                                                2                    OCH.sub.3   CH.sub.2 CN  O H  OCH.sub.3   NHCH.sub.3   CH                      OCH.sub.3   CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.3   CH.sub.2 CN  O H  OCH.sub.2 CF.sub.2 H                                                                       OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH 168-171°                                                                .                    OCH.sub.3   CH.sub.2 CN  O H  CH.sub.3    CH.sub.3     N                       OCH.sub.3   CH.sub.2 SCN O H  CH.sub.2 Br OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 SCN O H  OCH.sub.3   N(CH.sub.3).sub.2                                                                           N                       OCH.sub.3   CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 SCN O H  OCH.sub.3   SCH.sub.3    N                       OCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.2 CF.sub.3                                                                         CH.sub.3     CH                      OCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CF.sub.3     CH                      OCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.2 Cl CH.sub.3     CH                      OCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     N                       OCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  Cl          OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 N(CH.sub.3 ).sub.2                                                                 O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.3   CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  CH.sub.3    CH.sub.3     CH                      OCH.sub.3   CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  Cl          OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.3   CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  OCH.sub.3   CH.sub.3     N                       OCH.sub.3   CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.3   OCH.sub.3    CH 135-138              OCH.sub.3   CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.3   CH.sub.3     CH 101-110              OCH.sub.3   CH.sub.2 SeCH.sub.3                                                                         O H  Cl          OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 SeCH.sub.3                                                                         O H  CH.sub.3    CH.sub.3     CH 101-103              OCH.sub.3   CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.3   OCH.sub.3    N  101-105              OCH.sub.3   CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.3   CH.sub.3     N  120-127              OCH.sub.3   CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.2 CH.sub.3                                                                         NHCH.sub.3   N                       OCH.sub.3   CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH 142-144              OCH.sub.3   CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     CH 129-132              OCH.sub.3   CH.sub.2 N.sub.3                                                                            O H  Cl          OCH.sub.3    CH 144-146              OCH.sub.3   CH.sub.2 N.sub.3                                                                            O H  CH.sub.3    CH.sub.3     CH 137-142              OCH.sub.3   CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    N  137-142              OCH.sub.3   CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     N   96-101              OCH.sub.3   CH.sub.2 NO.sub.2                                                                           O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 NO.sub.2                                                                           O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 NO.sub.2                                                                           O H  Cl          OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 NO.sub.2                                                                           O H  CH.sub.3    CH.sub.3     CH                      OCH.sub.3   CH.sub.2 NO  O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.3   CH.sub.2 NO.sub.2                                                                           O H  OCH.sub.3   CH.sub.3     N                       OCH.sub.3   CH.sub.2 NC  O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3   CH.sub.2 NC  O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   SCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   OCH.sub. 3   CH                      OCH.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.2 CHCH.sub.2                                                                        N                       OCH.sub.2 CH.sub.3                                                                         CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH.sub.2 NO.sub.2                                                                           O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  OCH.sub.3   CH.sub.3     N                       OCH(CH.sub.3).sub.2                                                                        CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      o- -n-C.sub.4 H.sub.9                                                                      CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.2 C CH                                                                              N                       OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 SCN O H  CH.sub.3    OCH.sub.2 CH.sub.2 OCH.sub.3                                                                CH                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 NH(CH.sub.2 CH.sub.2 CH.sub.3)                                                     O H  OCH.sub.3   OCH.sub.3    CH                      OCF.sub.2 H CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      OCF.sub.2 H CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    N                       OCF.sub.2 H CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 SCH.sub.3                                                                          CH                      OCF.sub.2 H CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     N                       OCF.sub.2 H CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     CH                      OCF.sub.2 H CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      OCF.sub.2 H CH.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                         O H  OCH.sub.3   OCH.sub.3    N                       OCF.sub.2 H CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  CH.sub.3    CH.sub.3     CH                      OCH.sub.2 CH.sub.2 F                                                                       CH.sub.2 CN  O H  OCH.sub. 3  OCH.sub.3    CH                      OCH.sub.2 CH.sub.2 F                                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CF.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.3     N                       OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  I           OCH.sub.3    CH                      OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 SeCH.sub.3                                                                         O H  CH.sub.3    OCH.sub.3    CH                      OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CN  O H  OCH.sub.3   NH.sub.2     CH                      OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH CH.sub.2                                                                      CH.sub.2 CN  O H  CH.sub.3    NHCH.sub.2 CH.sub.2 CH.sub.3                                                                CH                      OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.2 C CH                                                                              CH                      OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 SeCH.sub.2 CH.sub.3                                                                O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 C CH                                                                             CH.sub.2 CN  O H  CH.sub.2 C.sub.3                                                                           OCH.sub.3    CH                      OCH.sub.2 C CH                                                                             CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.2 CH.sub.2 CH.sub.2CH.su                                               b.3          CH                      OCH.sub.2 C CH                                                                             CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 C CH                                                                             CH.sub.2 SCN O H  CH.sub.3    CH.sub.2 SCH.sub.3                                                                          CH                      OCH.sub.2 C CH                                                                             CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 C CH                                                                             CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    N                       OCH.sub.2 C CH                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.2 SCH.sub.2 CH.sub.2                                                    CH.sub.2     CH                      OCH.sub.2 C CH                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      OC(Cl)CHCl  CH.sub.2 CN  O H  OCH.sub.3   CH.sub.2 CH.sub.2 F                                                                         N                       OC(Cl)CHCl  CH.sub.2 CN  O H  I           OCH.sub.3    CH                      OC(Cl)CHCl  CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.2 C CH                                                                              CH                      OC(Cl)CHCl  CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   C CH         N                       OC(Cl)CHCl  CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub. 3   CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH 177-179              CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH 172-175              CO.sub.2 CH CH.sub.2 CN  O H  CH.sub.3    CH.sub.3     CH 174-177              CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N  160-163              CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  CH.sub.2 CH.sub.2                                                                          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  Cl          OCH.sub.3    CH 181-185              CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N  126-132              CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  Cl          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  CH.sub.3    CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH 126                  CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  NHCH.sub.3  OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   CH(OCH.sub.3).sub.2                                                                         CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N  oil                  CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH oil                  CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    CH.sub.3     CH oil                  CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     N  oil                  CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  cyclo-      OCH.sub.3    CH                                                    propyl                                           CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH oil                  CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.2 CF.sub.3                                                                          N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(S)(SCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(SCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH.sub.2                                                                           O H  cyclo-      OCH.sub.3    CH                                                    propyl                                           CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH.sub.2                                                                           O H  Cl          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH.sub.2                                                                           O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH.sub.2                                                                           O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  CH.sub.3    OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                  O H  Cl          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub. 3)                                                    O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH(CH(CH.sub.3).sub.2)                                                             O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                         O H  CH.sub.3    CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                         O H  OCH.sub.3   CH.sub.3     N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                         O H  Cl          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                            O H  Cl          OCH.sub.3    CH 136-141              CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.2 CH.sub.3                                                                         NHCH.sub.3   CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     N  117-118              CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                            O H  CH.sub.3    CH.sub.3     CH 174-176              CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH 159-160              CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                           O H  CH.sub.3    OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                           O H  CH.sub.3    CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                           O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                           O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                           O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                           O H  Cl          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NC  O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH.sub.2 NC  O H  CH.sub.3    OCH.sub.3    N                       CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH 132-136              CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    N                       CO.sub.2 CH.sub. 2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   N(OCH.sub.3)CH.sub.3                                                                        N                       CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH 160-164              CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     N  106-109              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.2 SCN O H  OCH.sub.3   CN           CH                      CO.sub.2 CH.sub.2 C CH                                                                     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.2 F                                                               CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.2 F                                                               CH.sub.2 SCN O H  CH.sub.3    CHO          CH                      CO.sub.2 CH.sub.2 CF.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub. 3                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   N.sub.3      CH                      CO.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3                                                       CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     N                       C(O)NHCH.sub.3                                                                             CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      C(O)NHCH.sub.3                                                                             CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      C(O)NHCH.sub.3                                                                             CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      C(O)NHCH.sub.3                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 CN  O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      C(O)(CH.sub.3).sub.2                                                                       CH.sub.2 SCN O H  Cl          OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 SeCH.sub.2 CH.sub.2 CH.sub.3                                                       O H  OCH.sub.3   OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      CHN(CH.sub.3).sub.2                                                                         O H  OCH.sub.3   CH(OCH.sub.3).sub.2                                                                         CH                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    N                       SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 SCN O H  Cl          OCH.sub.3    CH                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      SO.sub. 2 NHCH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 NHCH.sub.2 CH.sub.3                                                               CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 NHCH.sub.2 CH.sub.3                                                               CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 NHCH.sub.2 CH.sub.3                                                               CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 NHCH.sub.2 CH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 NHCH.sub.2 CH.sub.2 CH.sub.3                                                      CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                        CH.sub.2 SCN O H  Cl          OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3)(CH(CH.sub.3).sub.2)                                                   CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 N(CH.sub.3)(OCH.sub.3)                                                            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3)(OCH.sub.3)                                                            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 N(CH.sub.3 )(OCH.sub.3)                                                           CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3)(OCH.sub.3)                                                            CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CN  O H  CH.sub.3    OCH.sub.2 CHCH.sub.2                                                                        CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N                       SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 SCN O H  OCH.sub.3   N(CH.sub.3)(CH(CH.sub.3).sub.2)                                                             CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.2 C(CH.sub.3)CH.sub.2                                                               CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 NO.sub.2                                                                           O H  OCH.sub.3   CH.sub.2 S(CH.sub.2).sub.3                                                     CH.sub.3     N                       SO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   (CH.sub.2).sub.4 CH.sub.2                                                      SCH.sub.2 CH.sub.3                                                                          CH                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 CH.sub.3                                                                          C(O)H        O H  OCH.sub.3   OCH.sub.3    CH 166-168              SO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH 177-175              SO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   cyclopropyl  CH                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    N                       SO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   2-methylcyclo-                                                                              CH                                                                propyl                               SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N                       SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.3    C CH         CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   cyclopentyl  N                       SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH 157-158              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH 151-156              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  CH.sub.3    CH.sub.3     CH 160-162              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  Cl          OCH.sub.3    CH 151-160              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N  157-167              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N  206-208              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH 164-168              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     CH 157-159              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  CH.sub.3    CH.sub.3     CH 163-166              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  Cl          OCH.sub.3    CH 182-184              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    N  176-178              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     N  179-181              SCH.sub.3   CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      SCH.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       S(O)CH.sub.2 CH.sub.3                                                                      CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      S(O)CH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 P(O)(OCH.sub.3 ).sub.2                                                             O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N                       OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   CHO          CH                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   C CCH.sub.3  CH                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       OSO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    N                       OSO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   COCH.sub.3   CH                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   CH(OCH.sub.3).sub.2                                                                         CH                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N                       OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     N                       OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   CH(SCH.sub.3)(OCH.sub.2                                                        CH.sub.3)    CH                      OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      CH.sub.2 OCH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       CH.sub.2 SCH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    C(CH.sub.3)(SCH.sub.3).sub.2                                                                CH                      CH.sub.2 CH.sub.3 OCH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 CH.sub.2 OCH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       CH.sub.2 CH.sub.2 OCH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   1,3-dioxolan-2-yl                                                                           CH                      CH.sub.2 CN CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       C.sub.2 H.sub.5                                                                            CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      C.sub.2 H.sub.5                                                                            CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      C.sub.2 H.sub.5                                                                            CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       C.sub.2 H.sub.5                                                                            CH.sub.2 SCN O H  OCH.sub.3   2-methyl-1,3-                                                                               CH                                                                oxathion-2-yl                        COCH.sub.3  CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      COCH.sub.2 CH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    N                       COC CCH.sub.3                                                                              CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      COCH.sub.2 CH.sub.2 Cl                                                                     CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      C(O)cyclo-  CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       propyl                                                                         C(O)cyclo-  CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      propyl                                                                         C(O)cyclo-  CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      propyl                                                                         CH(OCH.sub.3).sub.2                                                                        CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       CH(OCH.sub.3).sub.2                                                                        CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      CH(OCH.sub.2 CH.sub.3).sub.2                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CH(OCH.sub.2 CH.sub.3).sub.2                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3     CH                      1,3-dioxyl-2-yl                                                                            CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3    CH                      1,3-dioxyl-2-yl                                                                            CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N                       R.sub.1A    CH.sub.2 CN  O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      R.sub.1A    CH.sub.2 CN  O H  OCH.sub.3   1,3-oxathion-2-yl                                                                           CH                      R.sub.1A    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1A    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1A    CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      R.sub.1A    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1A    CH.sub.2 SCN O H  CH.sub.3    2-methyl-1,3-                                                                               CH                                                                dithian-2-yl                         R.sub.1A    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1A    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1A    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1B    CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      R.sub.1B    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1B    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1B    CH.sub.2 CN  O H  OCH.sub.3   4-methyl-1,3-                                                                               CH                                                                dioxolan-2-yl                        R.sub.1B    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1B    CH.sub.2 SCN O H  Cl          OCH.sub.3    CH                      R.sub.1B    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1B    CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    N                       R.sub.1B    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1B    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                              O H  CH.sub.3    OCH.sub.3    CH                      R.sub.1C    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1C    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1C    CH.sub.2 CN  O H  OCH.sub.3   4-methyl-1,3-                                                                               CH                                                                oxathiolan-2-yl                      R.sub.1C    CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N                       R.sub.1C    CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3    CH                      R.sub.1C    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1C    CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      R.sub.1 C   CH.sub.2 P(O)(OMe).sub.2                                                                    O H  CH.sub.3    OCH.sub.3    CH                      R.sub.1C    CH.sub.2 P(O)(OMe).sub.2                                                                    O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1C    CH.sub.2 P(O)(OMe).sub.2                                                                    O H  CH.sub.2 CH.sub.3                                                                          OCH.sub.3    CH                      R.sub.1D    CH.sub.2 P(O)(OMe).sub.2                                                                    O H  OCH.sub.3   2,4-dimethyl-1,3-                                                                           CH                                                                dithiolan-2-yl                       R.sub.1D    CH.sub.2 P(O)(OMe).sub.2                                                                    O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1E    CH.sub.2 P(O)(OMe).sub.2                                                                    O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1F    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1G    CH.sub.2 CN  O H  OCH.sub.3   N(OCH.sub.3)CH.sub.3                                                                        CH                      R.sub.1H    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1I    CH.sub.2 CN  O H  CH.sub.3    CH.sub.3     CH                      R.sub.1J    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1K    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1L    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1M    CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3     CH                      R.sub.1N    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1O    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1P    CH.sub.2 CN  O H  Cl          OCH.sub.3    CH                      R.sub.1Q    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       R.sub.1R    CH.sub.2 P(O)(OMe).sub.2                                                                    O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1S    CH.sub.2 P(O)(OMe).sub.2                                                                    O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                            O H  CH.sub.3    CH.sub.3     CH 165-170              CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                            O H  Cl          OCH.sub.3    CH 146-148              CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  Cl          OCH.sub.3    CH 104-115              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH 149-150              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     CH 142-144              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                            O H  Cl          OCH.sub.3    CH 161-162              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                            O H  CH.sub.3    CH.sub.3     CH 171-173              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    N  133-134              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     N  125-127              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH 138-140              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  Cl          OCH.sub.3    CH                      CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  CH.sub.3    CH.sub.3     CH 167-169              CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N                       Cl          CH(CH.sub.3)CN                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3   CHFCN        O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH(CH.sub.2 CH.sub. 3)SCN                                                                   O H  CH.sub.3    CH.sub.3     CH                      NO.sub.2    CH(CH.sub.3)P(O)(OCH.sub.3).sub.2                                                           O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH(CH.sub.2 CH.sub.3)P(S)(CH.sub.3).sub.2                                                   O H  OCH.sub.3   CH.sub.3     N                       CO.sub.2 N(CH.sub.3).sub.2                                                                 CH(CH.sub.3)N(CH.sub.3).sub.2                                                               O H  Cl          OCH.sub.3    CH                      OCH.sub.3   CH(OC(O)CH.sub.3).sub.2                                                                     O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.3   CH(CH.sub.2 CH.sub.3)N.sub.3                                                                O H  OCH.sub.3   CH.sub.3     CH                      Cl          CH(CH.sub.3)SeCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH(CH.sub.2 CH.sub.3)N.sub.3                                                                O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                         O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                         O H  Cl          OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                         O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                         O H  OCH.sub.3   CH.sub.3     N                       OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)CN                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)CN                                                                              O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)CN                                                                              O H  OCH.sub.3   CH.sub.3     N                       CO.sub.2 CH.sub.3                                                                          CH(CH.sub.2 CH.sub.3)NC                                                                     O H  OCH.sub.3   OCH.sub.3    CH                      Cl          CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      NO.sub.2    CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH(OCH.sub.3).sub.2                                                                         O H  Cl          OCH.sub.3    CH                      OCH.sub.3   CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.3   CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                                                         O H  OCH.sub.3   CH.sub.3     N                       CO.sub.2 CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.3).sub.2                                                                O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  CH.sub.3    CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  Cl          OCH.sub.3    CH                      OCH.sub.3   C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                                O H  CH.sub.3    CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.2 CH.sub.3)(OCH.sub.3).sub.2                                                       O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          CH(SCH.sub.3).sub.3                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.2 CH.sub.3)(SCH.sub.3).sub.2                                                       O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3                                                                                   ##STR19##   O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH(CN)(OSi(CH.sub.3).sub.3)                                                                 O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          CH(CN)(OSi(CH.sub.3).sub.3)                                                                 O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(CN)OH                                                                           O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.2 CH.sub.3)(CN)OCH.sub.3                                                           O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          1,-3-dithiolan-2-yl                                                                         O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          1,-3-dithiolan-2-yl                                                                         O H  Cl          OCH.sub.3    CH                      Cl          1,-3-dithiolan-2-yl                                                                         O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                          O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                          O H  OCH.sub.3   CH.sub.3     CH                      NO.sub.2    1,-3-dioxolan-2-yl                                                                          O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          2-methyl-1,3-                                                                               O H  OCH.sub.3   OCH.sub.3    CH                                  dioxolan-2-yl                                                      CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                          O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                          O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                          O H  Cl          OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 1,-3-dithian-2-yl                                                                           O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                          2-methyl-1,3-                                                                               O H  OCH.sub.3   OCH.sub.3    CH                                  dioxan-2-yl                                                        C.sub.6 H.sub.5                                                                            CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH                      Cl                                                                                          ##STR20##   O H  OCH.sub.3   OCH.sub.3    CH                      NO.sub.2                                                                                    ##STR21##   O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                  ##STR22##   O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3                                                                                   ##STR23##   O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.3                                                                                   ##STR24##   O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.3                                                                                   ##STR25##   O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub. 2 CH.sub.3                                                                         ##STR26##   O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                          ##STR27##   O H  OCH.sub.3   OCH.sub.3    CH 192--192             OCH.sub.2 CH.sub.3                                                                          ##STR28##   O H  OCH.sub.3   CH.sub.3     N  188-190              OCH.sub.2 CH.sub.3                                                                          ##STR29##   O H  CH.sub.3    CH.sub.3     CH 180-181              OCH.sub.2 CH.sub.3                                                                          ##STR30##   O H  OCH.sub.3   CH.sub.3     CH 137-138              OCH.sub.2 CH.sub.3                                                                          ##STR31##   O H  Cl          OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                          ##STR32##   O H  OCH.sub.3   OCH.sub.3    N  135-136              OCH.sub.2 CH.sub.3                                                                          ##STR33##   O H  OCH.sub.3   OCH.sub.3    CH                      OCH.sub.2 CH.sub.3                                                                          ##STR34##   O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH.sub.3                                                                          ##STR35##   O H  Cl          OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                           ##STR36##   O H  OCH.sub.3   OCH.sub.3    CH 189-190              CO.sub.2 CH.sub.3                                                                           ##STR37##   O H  OCH.sub.3   CH.sub.3     CH 115                  CO.sub.2 CH.sub.3                                                                           ##STR38##   O H  Cl          OCH.sub.3    CH 182-184              CO.sub.2 CH.sub.3                                                                           ##STR39##   O H  OCH.sub.3   OCH.sub.3    N  174-175              CO.sub.2 CH.sub.3                                                                           ##STR40##   O H  OCH.sub.3   CH.sub.3     N  150-154              CO.sub.2 CH.sub.3                                                                           ##STR41##   O H  CH.sub.3    CH.sub.3     CH 145-147              CO.sub.2 CH.sub.3                                                                           ##STR42##   O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.3                                                                           ##STR43##   O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.3                                                                           ##STR44##   O H  OCH.sub.3   OCH.sub.3    N                       CO.sub.2 CH.sub.3                                                                           ##STR45##   O H  OCH.sub.3   CH.sub.3     N                       CO.sub.2 CH.sub.2 CH.sub. 3                                                                 ##STR46##   O H  OCH.sub.3   OCH.sub.3    CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR47##   O H  OCH.sub.3   CH.sub.3     CH                      CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR48##   O H  Cl          OCH.sub.3    CH 123-124              OSO.sub.2 CH.sub.3                                                                          ##STR49##   O H  OCH.sub.3   CH.sub.3     CH                      SO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR50##   O H  OCH.sub.3   OCH.sub.2 CH.sub.3                                                                          CH                      C(O)N(CH.sub.2 CH.sub.3).sub.2                                                             Cl           O H  CH.sub.3    CH.sub.3     CH 180-183              Cl          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH 150-152              Cl          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     CH 138-139              Cl          CH.sub.2 N.sub.3                                                                            O H  CH.sub.3    CH.sub.3     CH 167-170              Cl          CH.sub.2 N.sub.3                                                                            O H  Cl          OCH.sub.3    CH 145-147              Cl          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    N  134-137              Cl          CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     N  oil                  CO.sub.2 CH.sub. 2 CH.sub.3                                                                 ##STR51##   O H  OCH.sub.3   OCH.sub.3    CH 144-146              CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR52##   O H  CH.sub.3    CH.sub.3     CH 144-146              CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR53##   O H  OCH.sub.3   OCH.sub.3    N  146-148              CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR54##   O H  OCH.sub.3   CH.sub.3     N  142-145              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    CH 128                  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     CH 131-132              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  CH.sub.3    CH.sub.3     CH 144-147              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  Cl          OCH.sub.3    CH 156-158              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   OCH.sub.3    N  134-135              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                            O H  OCH.sub.3   CH.sub.3     N  oil                  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    CH 130-131              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     CH 144-145              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  CH.sub.3    CH.sub.3     CH 150-152              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  Cl          OCH.sub.3    CH 178-181              CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3    N  oil                  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3     N  oil                  CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH 171-174              CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   CH.sub.3     CH 188-190              CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  CH.sub.3    CH.sub.3     CH 182-185              CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  Cl          OCH.sub.3    CH 185-188              CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub. 3   N  167-169              CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   CH.sub.3     N  136-138              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH 170-171              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   CH.sub.3     CH 183-185              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  CH.sub.3    CH.sub.3     CH 180-182              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  Cl          OCH.sub.3    CH 115-118              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    N   95-100              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   CH.sub.3     N  112-116              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH 185-187              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   CH.sub.3     CH                      OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    N                       OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   CH.sub.3     N                       F           CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      F           CH NOCH.sub.3                                                                               O H  OCH.sub.3   OCH.sub.3    CH                      F           C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      F           C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      Cl          CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      Cl          CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      Cl          C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      Cl          C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      NO.sub.2    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      NO.sub.2    CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      NO.sub.2    C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      NO.sub.2    C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.3    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.3    CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.3    C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.3    C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      C(O)N(CH.sub.3).sub.2                                                                      C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 N(CH.sub.3).sub.2                                                                 C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.3                                                                          CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.3                                                                          C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      SO.sub.2 CH.sub.3                                                                          CH(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.3                                                                         CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.3                                                                         CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      OSO.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  OCH.sub. 3  OCH.sub.3    CH                      OSO.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 OCH.sub.3                                                                         CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 OCH.sub.3                                                                         CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 OCH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 OCH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 SCH.sub.3                                                                         CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 SCH.sub.3                                                                         CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 SCH.sub.3                                                                         C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 SCH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 CN CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 CN CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 CN C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CH.sub.2 CN C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      CH(OCH.sub.3).sub.2                                                                        CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      CH(OCH.sub.3).sub.2                                                                        CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3    CH                      CH(OCH.sub.3).sub.2                                                                        C(CH.sub.3)NOH                                                                              O H  OCH.sub.3   OCH.sub.3    CH                      CH(OCH.sub.3).sub.2                                                                        C(CH.sub.3)NOCH.sub.3                                                                       O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1A    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1B    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1C    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1D    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1E    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1F    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1G    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1H    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1I    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1J    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1K    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1L    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1M    CHNOH        O H  OCH.sub. 3  OCH.sub.3    CH                      R.sub.1N    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1O    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1P    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1Q    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1R    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      R.sub.1S    CHNOH        O H  OCH.sub.3   OCH.sub.3    CH                      __________________________________________________________________________

                  TABLE II                                                         ______________________________________                                         General Formula II                                                                                                     m.p.                                   R.sub.1   R.sub.2        X.sub.1   Y.sub.1                                                                             (°C.)                           ______________________________________                                         F         CH.sub.2 CN    CH.sub.3  O                                           Cl.sub.3  CH.sub.2 SCN   OCH.sub.3 O                                           CF.sub.3  CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                       OCH.sub.3 CH.sub.2                                    NO.sub.2  CH.sub.2 CN    OCH.sub.3 O                                           OCH.sub.3 CH.sub.2 CN    OCH.sub.3 O                                           OCH.sub.3 CH.sub.2 SCN   OCH.sub.3 CH.sub.2                                    OCH.sub.2 CH.sub.3                                                                       CH.sub.2 SCN   OCH.sub.3 O                                           OCH.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.3 CH.sub.2                                    CO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCF.sub.2 H                                                                              O                                           CO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCH.sub.3 CH.sub.2                                    CO.sub.2 CH.sub.3                                                                        CH.sub.2 SCN   OCH.sub.3 O                                           CO.sub.2 CH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 O                                           CO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 O                                           CO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 CN    OCH.sub.3 CH.sub.3                                    CO.sub.2 N(CH.sub. 3).sub.2                                                              CH.sub.2 CN    CH.sub.3  O                                           SO.sub.2 NHCH.sub.3                                                                      CH.sub.2 CN    OCH.sub.3 O                                           SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.2 CN    OCH.sub.3 CH.sub.2                                    SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.2 SCN   OCH.sub.3 O                                           SO.sub.2 CH.sub.3                                                                        CH.sub.2 SCN   OCH.sub.3 O                                           SO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCF.sub.2 H                                                                              CH.sub.2                                    SO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 CN    OCH.sub.3 O                                           SO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 O                                           OSO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 CH.sub.2                                    OSO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.2 CH.sub.3                                                                       O                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 SCN   OCH.sub.3 O                                           R.sub.1 --A                                                                              CH.sub.2 CN    CH.sub.3  O                                           R.sub.1 --A                                                                              CH.sub.2 SCN   OCH.sub.3 CH.sub.2                                    R.sub.1 --B                                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 O                                           R.sub.1 --C                                                                              CH.sub.2 CN    OCH.sub.3 O                                           F         CH═NOH     CH.sub.3  O                                           OCH.sub.3 CH═NOH.sub.3                                                                              OCH.sub.3 O                                           COOCH.sub.3                                                                              C(CH.sub.3)═NOH                                                                           OCF.sub.2 H                                                                              CH.sub.2                                    CO.sub.2 N(CH.sub.3).sub.2                                                               C(CH.sub.3)═NOCH.sub.3                                                                    CH.sub.3  O                                           SO.sub.2 N(CH.sub.3).sub.2                                                               CH═NOH     OCH.sub.3 O                                           SO.sub.2 CH.sub.3                                                                        CH═NOCH.sub.3                                                                             OCH.sub.3 CH.sub.2                                    OSO.sub.2 CH.sub.2 CH.sub.3                                                              C(CH.sub.3)═NOH                                                                           OCF.sub.2 H                                                                              O                                           R.sub.1 --A                                                                              C(CH.sub.3)═NOCH.sub.3                                                                    CH.sub.3  O                                           R.sub.1 --B                                                                              CH═NOH     CH.sub.3  CH.sub.2                                    R.sub.1 --C                                                                              CH═NOCH.sub.3                                                                             OCH.sub.3 O                                           ______________________________________                                    

                  TABLE III                                                        ______________________________________                                         General Formula III                                                            R.sub.1   R.sub.2        X.sub.1   m.p. (°C.)                           ______________________________________                                         F         CH.sub.2 CN    CH.sub.3                                              Cl        CH.sub.2 SCN   OCH.sub.3                                             CF.sub.3  CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                       OCH.sub.3                                             NO.sub.2  CH.sub.2 CN    OCH.sub.3                                             OCH.sub.3 CH.sub.2 CN    OCH.sub.3                                             OCH.sub.3 CH.sub.2 SCN   OCH.sub.3                                             OCH.sub.2 CH.sub.3                                                                       CH.sub.2 SCN   OCH.sub.3                                             OCH.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.3                                             CO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCF.sub.2 H                                           CO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCH.sub.3                                             CO.sub.2 CH.sub.3                                                                        CH.sub.2 SCN   OCH.sub.3                                             CO.sub.2 CH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                             CO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                             CO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 CN    OCH.sub.3                                             CO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.2 CN    CH.sub.3                                              SO.sub.2 NHCH.sub.3                                                                      CH.sub.2 CN    OCH.sub.3                                             SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.2 CN    OCH.sub.3                                             SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.2 SCN   OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                        CH.sub. 2 SCN  OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCF.sub.2 H                                           SO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 CN    OCH.sub.3                                             SO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                             OSO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                             OSO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.2 CH.sub.3                                    OSO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 SCN   OCH.sub.3                                             R.sub.1 --A                                                                              CH.sub.2 CN    CH.sub.3                                              R.sub.1 --A                                                                              CH.sub.2 SCN   OCH.sub.3                                             R.sub.1 --B                                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                             R.sub.1 --C                                                                              CH.sub.2 CN    OCH.sub.3                                             F         CH═NOH     CH.sub.3                                              OCH.sub.3 CH═NOCH.sub.3                                                                             OCH.sub.3                                             COOCH.sub.3                                                                              C(CH.sub.3)═NOH                                                                           OCH.sub.3                                             CO.sub.2 N(CH.sub.3).sub.2                                                               C(CH.sub.3)═NOCH.sub.3                                                                    OCF.sub.2 H                                           SO.sub.2 N(CH.sub.3).sub.2                                                               CH═NOH     CH.sub.3                                              SO.sub.2 CH.sub.3                                                                        CH═NOCH.sub.3                                                                             OCH.sub.3                                             OSO.sub.2 CH.sub.2 CH.sub.3                                                              C(CH.sub.3)═NOH                                                                           CH.sub.3                                              R.sub.1 --A                                                                              C(CH.sub.3)═NOCH.sub.3                                                                    OCH.sub.3                                             R.sub.1 --B                                                                              CH═NOH     OCF.sub.2 H                                           R.sub.1 -- C                                                                             CH═NOCH.sub.3                                                                             OCH.sub.3                                             ______________________________________                                    

                  TABLE IV                                                         ______________________________________                                         General Formula IV                                                                                                     m.p.                                   R.sub.1   R.sub.2        X.sub.1   Y.sub.3                                                                             (°C.)                           ______________________________________                                         F         CH.sub.2 CN    CH.sub.3  H                                           Cl        CH.sub.2 SCN   OCH.sub.3 H                                           CF.sub.3  CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                       OCH.sub.3 CH.sub.3                                    NO.sub.2  CH.sub.2 CN    OCH.sub.3 H                                           OCH.sub.3 CH.sub.2 CN    OCH.sub.3 H                                           OCH.sub.3 CH.sub.2 SCN   OCH.sub.3 CH.sub.3                                    OCH.sub.2 CH.sub.3                                                                       CH.sub.2 SCN   OCH.sub.3 H                                           OCH.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.3 CH.sub.3                                    CO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCF.sub.2 H                                                                              H                                           CO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCH.sub.3 CH.sub.3                                    CO.sub.2 CH.sub.3                                                                        CH.sub.2 SCN   OCH.sub.3 H                                           CO.sub.2 CH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 H                                           CO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 H                                           CO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 CN    OCH.sub.3 CH.sub.3                                    CO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.2 CN    CH.sub.3  H                                           SO.sub.2 NHCH.sub.3                                                                      CH.sub.2 CN    OCH.sub. 3                                                                               H                                           SO N(CH.sub.3).sub.2                                                                     CH.sub.2 CN    OCH.sub.3 H                                           SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.2 SCN   OCH.sub.3 H                                           SO.sub.2 CH.sub.3                                                                        CH.sub.2 SCN   OCH.sub.3 H                                           SO.sub.2 CH.sub.3                                                                        CH.sub.2 CN    OCF.sub.2 H                                                                              CH.sub.3                                    SO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 CN    OCH.sub.3 H                                           SO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 H                                           OSO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 CH.sub.3                                    OSO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.2 CH.sub.3                                                                       H                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 SCN   OCH.sub.3 H                                           R.sub.1 --A                                                                              CH.sub.2 CN    CH.sub.3  H                                           R.sub.1 --A                                                                              CH.sub.2 SCN   OCH.sub.3 CH.sub.3                                    R.sub.1 --B                                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3 H                                           R.sub.1 --C                                                                              CH.sub.2 CN    OCH.sub.3 H                                           F         CH═NOH     CH.sub.3  H                                           OCH.sub.3 CH═NOH.sub.3                                                                              CH.sub.3  CH.sub.3                                    COOCH.sub.3                                                                              C(CH.sub.3)═NOH                                                                           OCH.sub.3 H                                           CO.sub.2 N(CH.sub.3).sub.2                                                               C(CH.sub.3)═NOCH.sub.3                                                                    OCH.sub.3 H                                           SO.sub.2 N(CH.sub.3).sub.2                                                               CH═NOH     CH.sub.3  H                                           SO.sub.2 CH.sub.3                                                                        CH═NOCH.sub.3                                                                             CH.sub.3  CH.sub.3                                    OSO.sub.2 CH.sub.2 CH.sub.3                                                              C(CH.sub.3)═NOH                                                                           CH.sub.3  H                                           R.sub.1 --A                                                                              C(CH.sub.3)NOCH.sub.3                                                                         OCH.sub.3 H                                           R.sub.1 --B                                                                              CH═NOH     CH.sub.3  CH.sub.3                                    R.sub.1 --C                                                                              CH═NOCH.sub.3                                                                             OCH.sub.3 H                                           ______________________________________                                    

                                      TABLE V                                      __________________________________________________________________________     General Formula V                                                              R.sub.1  R.sub.2     X.sub.2                                                                              Y.sub.2                                                                              m.p. (°C.)                             __________________________________________________________________________     F        CH.sub.2 CN CH.sub.3                                                                             OCH.sub.3                                           Cl       CH.sub.2 SCN                                                                               CH.sub.3                                                                             OCH.sub.2 CH.sub.3                                  CF.sub.3 CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                    CH.sub.3                                                                             OCH.sub.3                                           NO.sub.2 CH.sub.2 CN CH.sub.3                                                                             SCH.sub.3                                           OCH.sub.3                                                                               CH.sub.2 CN CH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           OCH.sub.3                                                                               CH.sub.2 SCN                                                                               CH.sub.3                                                                             SCH.sub.2 CH.sub.3                                  OCH.sub.2 CH.sub.3                                                                      CH.sub.2 SCN                                                                               CH.sub.3                                                                             OCH.sub.3                                           OCH.sub.2 CH.sub.3                                                                      CH.sub.2 CN CH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN CH.sub.3                                                                             CH.sub.3                                            CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN CH.sub.3                                                                             OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN                                                                               CH.sub.3                                                                             CH.sub.2 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             CH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             CH.sub.3                                                                             OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN CH.sub.3                                                                             OCH.sub.2 CH.sub.3                                  CO.sub. 2 N(CH.sub.3).sub.2                                                             CH.sub.2 CN CH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           SO.sub.2 NHCH.sub.3                                                                     CH.sub.2 CN CH.sub.3                                                                             OCH.sub.3                                           SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN CH.sub.3                                                                             SCH.sub.3                                           SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 SCN                                                                               CH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           SO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN                                                                               CH.sub.3                                                                             OCH.sub.3                                           SO.sub.2 CH.sub.3                                                                       CH.sub.2 CN CH.sub.3                                                                             SCH.sub.2 CH.sub.3                                  SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN CH.sub.3                                                                             OCH.sub.3                                           SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             CH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           OSO.sub.2 CH.sub.3                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             CH.sub.3                                                                             CH.sub.3                                            OSO.sub.2 CH.sub.3                                                                      CH.sub.2 CN CH.sub.3                                                                             OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 SCN                                                                               CH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           R.sub.1 --A                                                                             CH.sub.2 CN CH.sub.3                                                                             OCH.sub.3                                           R.sub.1 --A                                                                             CH.sub.2 SCN                                                                               CH.sub.3                                                                             CH.sub.2 CH.sub.3                                   R.sub.1 --B                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             CH.sub.3                                                                             OCH.sub.3                                           R.sub.1 --C                                                                             CH.sub.2 CN CH.sub.3                                                                             OCH.sub.3                                           F        CH═NOH  CH.sub.3                                                                             OCH.sub.3                                           OCH.sub.3                                                                               CH═NOHCH.sub.3                                                                         CH.sub.3                                                                             CH.sub.3                                            COOCH.sub.3                                                                             C(CH.sub.3)═NOH                                                                        CH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           CO.sub.2 N(CH.sub.3).sub.2                                                              C(CH.sub.3)═NOCH.sub.3                                                                 CH.sub.2 CF.sub.3                                                                    CH.sub.3                                            SO.sub.2 N(CH.sub.3).sub.2                                                              CH═NOH  CH.sub.3                                                                             OCH.sub.2 CH.sub.3                                  SO.sub.2 CH.sub.3                                                                       CH═NOCH.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                             C(CH.sub.3)═NOH                                                                        CH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           R.sub.1 --A                                                                             C(CH.sub.3)═NOCH.sub.3                                                                 CH.sub.2 CH.sub.3                                                                    CH.sub.3                                            R.sub.1 --B                                                                             CH═NOH  CH.sub.3                                                                             OCH.sub.3                                           R.sub.1 -C                                                                              CH═NOCH.sub.3                                                                          CH.sub.3                                                                             CH.sub.3                                            __________________________________________________________________________

                  TABLE VI                                                         ______________________________________                                         General Formula VI                                                             R.sub.1    R.sub.2         X.sub.3 m.p. (°C.)                           ______________________________________                                         F          CH.sub.2 CN     OCH.sub.3                                           Cl         CH.sub.2 SCN    OCH.sub.3                                           CF.sub.3   CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                        OCH.sub.3                                           NO.sub.2   CH.sub.2 CN     CH.sub.3                                            OCH.sub.3  CH.sub.2 CN     OCH.sub.3                                           OCH.sub.3  CH.sub.2 SCN    CH.sub.3                                            OCH.sub.2 CH.sub.3                                                                        CH.sub.2 SCN    OCH.sub.3                                           OCH.sub.2 CH.sub.3                                                                        CH.sub.2 CN     CH.sub.3                                            CO.sub.2 CH.sub.3                                                                         CH.sub.2 CN     OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                         CH.sub.2 CN     CH.sub.3                                            CO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN    OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                 CH.sub.3                                            CO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                 OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN     CH.sub.3                                            CO.sub.2 N(CH.sub.3).sub.2                                                                CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 NHCH.sub.3                                                                       CH.sub.2 CN     CH.sub.3                                            SO.sub.2 N(CH.sub.3).sub.2                                                                CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 N(CH.sub.3).sub. 2                                                               CH.sub.2 SCN    CH.sub.3                                            SO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN    OCH.sub.3                                           SO.sub.2 CH.sub.3                                                                         CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN     CH.sub.3                                            SO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                 OCH.sub.3                                           OSO.sub.2 CH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                 CH.sub.3                                            OSO.sub.2 CH.sub.3                                                                        CH.sub.2 CN     OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 SCN    OCH.sub.3                                           R.sub.1 --A                                                                               CH.sub.2 CN     CH.sub.3                                            R.sub.1 --A                                                                               CH.sub.2 SCN    OCH.sub.3                                           R.sub.1 --B                                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                 CH.sub.3                                            R.sub.1 --C                                                                               CH.sub.2 CN     OCH.sub.3                                           F          CH═NOH      OCH.sub.3                                           OCH.sub.3  CH═NOCH.sub.3                                                                              OCH.sub.3                                           COOCH.sub.3                                                                               C(CH.sub.3)═NOH                                                                            CH.sub.3                                            CO.sub.2 N(CH.sub.3).sub.2                                                                C(CH.sub.3)═NOCH.sub.3                                                                     CH.sub.3                                            SO.sub.2 CH.sub.3                                                                         CH═NOH      OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                               C(CH.sub.3)═NOCH.sub.3                                                                     OCH.sub.3                                           R.sub.1 --A                                                                               C(CH.sub.3)═NOH                                                                            OCH.sub.3                                           R.sub.1 --B                                                                               C(CH.sub.3)═NOCH.sub.3                                                                     CH.sub.3                                            R.sub.1 --C                                                                               CH═NOH      OCH.sub.3                                           ______________________________________                                    

                                      TABLE VII                                    __________________________________________________________________________     General Formula VII                                                            R.sub.1 R.sub.2     X.sub.4                                                                               Y.sub.4                                                                              m.p. (°C.)                             __________________________________________________________________________     F       CH.sub.2 CN CH.sub.3                                                                              OCH.sub.3                                           Cl      CH.sub.2 SCN                                                                               OCH.sub.3                                                                             CH.sub.3                                            CF.sub.3                                                                               CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                    OCH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           NO.sub.2                                                                               CH.sub.2 CN CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                           OCH.sub.3                                                                              CH.sub.2 CN Cl     OCH.sub.3                                           OCH.sub.3                                                                              CH.sub.2 SCN                                                                               CH.sub.3                                                                              OCH.sub.2 CH.sub.3                                  OCH.sub.2 CH.sub.3                                                                     CH.sub.2 SCN                                                                               OCH.sub.3                                                                             OCH.sub.3                                           OCH.sub.2 CH.sub.3                                                                     CH.sub.2 CN OCH.sub.3                                                                             Cl                                                  CO.sub.2 CH.sub.3                                                                      CH.sub.2 CN CH.sub.3                                                                              OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                      CH.sub.2 CN OCH.sub.3                                                                             OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                      CH.sub.2 SCN                                                                               OCH.sub.3                                                                             CH.sub.3                                            CO.sub.2 CH.sub.3                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             OCH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             OCH.sub.3                                                                             OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN OCH.sub.3                                                                             OCH.sub.2 CH.sub.3                                  CO.sub.2 N(CH.sub.3).sub.2                                                             CH.sub.2 CN CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                           SO.sub.2 NHCH.sub.3                                                                    CH.sub.2 CN OCH.sub.3                                                                             CH.sub.3                                            SO.sub.2 N(CH.sub.3).sub.2                                                             CH.sub.2 CN OCH.sub.3                                                                             OCH.sub.3                                           SO.sub.2 N(CH.sub.3).sub.2                                                             CH.sub.2 SCN                                                                               Cl     OCH.sub.3                                           SO.sub.2 CH.sub.3                                                                      CH.sub.2 SCN                                                                               OCH.sub.3                                                                             CH.sub.3                                            SO.sub.2 CH.sub.3                                                                      CH.sub.2 CN OCH.sub.3                                                                             OCH.sub.3                                           SO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN OCH.sub.3                                                                             OCH.sub.3                                           SO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             CH.sub.3                                                                              OCH.sub.3                                           OSO.sub.2 CH.sub.3                                                                     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             OCH.sub.3                                                                             OCH.sub.2 CH.sub.3                                  OSO.sub.2 CH.sub.3                                                                     CH.sub.2 CN OCH.sub.3                                                                             OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                            CH.sub.2 SCN                                                                               OCH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           R.sub.1 --A                                                                            CH.sub.2 CN OCH.sub.3                                                                             OCH.sub.3                                           R.sub.1 --A                                                                            CH.sub.2 SCN                                                                               OCH.sub.3                                                                             CH.sub.3                                            R.sub.1 --B                                                                            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                           R.sub.1 --C                                                                            CH.sub.2 CN OCH.sub.3                                                                             OCH.sub.3                                           F       CH═NOH  CH.sub.3                                                                              OCH.sub.3                                           OCH.sub.3                                                                              CH═NOCH.sub.3                                                                          OCH.sub.3                                                                             CH.sub. 3                                           COOCH.sub.3                                                                            C(CH.sub.3)═NOH                                                                        OCH.sub.2 CH.sub.3                                                                    OCH.sub.3                                           CO.sub.2 N(CH.sub.3).sub.2                                                             C(CH.sub.3)═NOCH.sub.3                                                                 CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                           SO.sub.2 CH.sub.3                                                                      CH═NOH.sub.3                                                                           Cl     OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                            C(CH.sub.3)═NOCH.sub.3                                                                 CH.sub.3                                                                              OCH.sub.2 CH.sub.3                                  R.sub.1 --A                                                                            C(CH.sub.3)═NOH                                                                        OCH.sub.3                                                                             OCH.sub.3                                           R.sub.1 --B                                                                            CH(CH.sub.3)═NOCH.sub.3                                                                OCH.sub.3                                                                             Cl                                                  R.sub.1 --C                                                                            CH═NOH  CH.sub.3                                                                              OCH.sub.3                                           __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

    ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositons                                                                    ______________________________________                                          *Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are somtimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York. 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 10 High Strength Concentrate

5-(cyanomethyl)-2-methoxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide: 99%

trimethylnonyl polyethylene glycol ether: 1%

The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a U.S. S. No. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.

EXAMPLE 11 Wettable Powder

5-(cyanomethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxybenzenesulfonamide: 65%

dodecylphenol polyethylene glycol ether: 2%

sodium ligninsulfonate: 4%

sodium silicoaluminate: 6%

montmorillonite (calcined): 23%

The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 12 Aqueous Suspension

5-(cyanomethyl)-2-methoxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide: 50.0%

polyacrylic acid thickener: 0.3%

dodecylphenol polyethylene glycol ether: 0.5%

disodium phosphate: 1%

monosodium phosphate: 0.5%

polyvinyl alcohol: 1.0%

water: 56.7%

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 13 Oil Suspension

5-(cyanomethyl)-2-methoxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide: 35%

blend of polyalcohol carboxylic esters and oil soluble petroleum sulfonates: 6%

xylene: 59%

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 14 Oil Suspension

5-(cyanomethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxybenzenesulfonamide: 25%

polyoxyethylene sorbitol hexaoleate: 5%

highly aliphatic hydrocarbon oil: 70%

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 15 Aqueous Suspension

5-(cyanomethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-methoxybenzenesulfonamide: 25%

hydrated attapulgite: 3%

crude calcium ligninsulfonate: 10%

sodium dihydrogen phosphate: 0.5%

water: 61.5%

The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns.

EXAMPLE 16 Wettable Powder

5-(cyanomethyl)-2-methoxy-N[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide: 40%

dioctyl sodium sulfosuccinate: 1.5%

sodium ligninsulfonate: 3%

low viscosity methyl cellulose: 1.5%

attapulgite: 54%

The ingredients are thoroughly blende, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

All compounds of the invention may be formulated in the same manner.

EXAMPLE 17 Granule

wettable powder of Example 16: 15%

gypsum: 69%

potassium sulfate: 16%

The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S. #18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain % active ingredient.

EXAMPLE 18 Wettable Powder

5-(cyanomethyl)-N-[(4,6-diemthoxypyrimidin-2-yl)-aminocarbonyl]-2-methoxybenzenesulfonamide: 50%

sodium alkylnaphthalenesulfonate: 2%

low viscosity methyl cellulose: 2%

diatomaceous earth: 46%

The ingredients are blended, coarsely hammer-milled and the air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 19 Extruded Pellet

5-(cyanomethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxybenzenesulfonamide: 25%

anhydrous sodium sulfate: 10%

crude calcium ligninsulfonate: 5%

sodium alkylnaphthalenesulfonate: 1%

calcium/magnesium bentonite: 59%

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 20 Wettable Powder

5-(cyanomethyl)-2-methoxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide: 80%

sodium alkylnaphthalenesulfonate: 2%

sodium ligninsulfonate: 2%

synthetic amorphous silica: 3%

kaolinite: 13%

The ingredients are blended and then ground in a hammermill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged.

EXAMPLE 21 High Strength Concentrate

5-(cyanomethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-methoxybenzenesulfonamide: 98.5%

silica aerogel: 0.5%

synthetic amorphous fine silica: 1.0%

The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.

Utility

Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as wheat. Alternatively, the subject compounds are useful to modify plant growth.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage pre-sent, etc. In general terms, the subject compounds should be applied at levels of around 0.001 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide; examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), cheatgrass (Bromus Secalinus), giant foxtail (Setaria faberii), wild oats (Avena fatua), velvetleaf (Abutilon theophrasti), morningglory (Ipomoea spp., cocklebur (Xanthium pensylvanicum), sorghum, corn, barley, soybean, sugarbeet, cotton, rice, wheat and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

B=burn;

C=chlorosis/necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation;

X=axillary stimulation;

S=albinism; and

6Y=abscised buds or flowers.

    __________________________________________________________________________     COMPOUNDS                                                                       ##STR55##                                                                     Compound                                                                              R.sub.1    R.sub.2   X    Y   Z                                         __________________________________________________________________________     1      OCH.sub.3  CH.sub.2 CN                                                                              CH.sub.3                                                                            OCH.sub.3                                                                          CH                                        2      OCH.sub.3  CH.sub.2 CN                                                                              OCH.sub.3                                                                           CH.sub.3                                                                           N                                         3      CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        4      CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           CH.sub.3                                                                            CH.sub.3                                                                           CH                                        5      CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         6      CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           OCH.sub.3                                                                           CH.sub.3                                                                           N                                         7      CO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN                                                                             OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        8      CO.sub.2 CH.sub.3                                                                         CH.sub.2 CN                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        9      CO.sub.2 CH.sub.3                                                                         CH.sub.2 CN                                                                              OCH.sub.3                                                                           CH.sub.3                                                                           N                                         10     OCH.sub.3  CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        11     OCH.sub.3  CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        12     OCH.sub.3  CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                                                           CH                                        13     OCH.sub.3  CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           Cl  CH                                        14     OCH.sub.3  CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         15     OCH.sub.3  CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           CH.sub.3                                                                           N                                         16     OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        17     OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        18     OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH                                        19     OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         20     OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                           N                                         21     COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        22     COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        23     COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                                                           CH                                        24     COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         Cl   OCH.sub.3                                                                          CH                                        25     COOCH(CH.sub.3).sub.2                                                                     CH.sub. 2 N.sub.3                                                                        OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         26     COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           CH.sub.3                                                                           N                                         27     Cl         CH.sub.2 SCN                                                                             CH.sub.3                                                                            OCH.sub.3                                                                          CH                                        28     Cl         CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        29     Cl         CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                          CH                                        30     Cl         CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                                                           CH                                        31     Cl         CH.sub.2 N.sub.3                                                                         Cl   OCH.sub.3                                                                          CH                                        32     Cl         CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         33     Cl         CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           CH.sub.3                                                                           N                                         34     SO.sub.2 CH.sub.3                                                                         C(O)H     OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        35     SO.sub.2 CH.sub.3                                                                         CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        36     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        37     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                          CH                                        38     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           CH.sub.3                                                                           N                                         39     COOCH.sub.3                                                                               CH.sub.2 CN                                                                              OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        40     COOCH.sub.3                                                                               CH.sub.2 CN                                                                              CH.sub.3                                                                            CH.sub.3                                                                           CH                                        41     COOCH.sub. 3                                                                              CH.sub.2 CN                                                                              Cl   OCH.sub.3                                                                          CH                                        42     COOCH.sub.3                                                                               CH.sub.2 CN                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         43     COOCH.sub.2 CH.sub.3                                                                      C(O)H     OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        44     COOCH.sub.2 CH.sub.3                                                                      C(O)H     CH.sub.3                                                                            CH.sub.3                                                                           CH                                        45     COOCH.sub.2 CH.sub.3                                                                      C(O)H     Cl   OCH.sub.3                                                                          CH                                        46     COOCH.sub.2 CH.sub.3                                                                      C(O)H     OCH.sub.3                                                                           CH.sub.3                                                                           N                                         47     COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 CN                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        48     COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 CN                                                                              CH.sub.3                                                                            CH.sub.3                                                                           CH                                        49     COOCH.sub.3                                                                               C(O)H     OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        50     COOCH.sub.3                                                                               C(O)H     OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        51     COOCH.sub.3                                                                               C(O)H     CH.sub.3                                                                            CH.sub.3                                                                           CH                                        52     COOCH.sub.3                                                                               C(O)H     Cl   OCH.sub.3                                                                          CH                                        53     COOCH.sub.3                                                                               C(O)H     OCH.sub.3                                                                           CH.sub.3                                                                           N                                         54     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        55     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        56     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                                                           CH                                        57     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         Cl   OCH.sub.3                                                                          CH                                        58     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         59     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                           CH.sub.3                                                                           N                                         60     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        61     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        62     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              CH.sub.3                                                                            CH.sub.3                                                                           CH                                        63     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              Cl   OCH.sub.3                                                                          CH                                        64     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         65     COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              OCH.sub.3                                                                           CH.sub.3                                                                           N                                         66     OCH.sub.2 CH.sub.2                                                                        C(CH.sub.3)NOH                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        67     OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOH                                                                           OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        68     OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOH                                                                           Cl   OCH.sub.3                                                                          CH                                        69     OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOH                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         70     OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOH                                                                           OCH.sub.3                                                                           CH.sub.3                                                                           N                                         71     OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOCH.sub.3                                                                    OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        72     COOCH.sub.3                                                                               CHNOCH.sub.3                                                                             OCH.sub.3                                                                           OCH.sub.3                                                                          CH                                        73     COOCH.sub.3                                                                               CHNOCH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                           CH                                        74     COOCH.sub.3                                                                               CHNOCH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH                                        75     COOCH.sub.3                                                                               CHNOCH.sub.3                                                                             Cl   OCH.sub.3                                                                          CH                                        76     COOCH.sub.3                                                                               CHNOCH.sub.3                                                                             OCH.sub.3                                                                           OCH.sub.3                                                                          N                                         77     COOCH.sub.3                                                                               CHNOCH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                           N                                         __________________________________________________________________________

    TABLE A        Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6      Compound 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12      Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05      0.05      POST-EMERGENCE Morningglory 10C 4C,8H 10C 3C,9G 2C,3H 2C,2G      10C 10C 10C 4G 3C,8H 0 Cocklebur 9C 4C,9G 10C 2C,7G 2G 2G 9C 10C 10C 7G      7H 2H Velvetleaf 9C 2C,5G 10C 3C,7H 2H 2G 10C 10C 10C 4C,9G 3C,8H 3G      Nutsedge 2C,8G 2C,5G 4C,9G 5G 0 0 9G 9C 5C,9G 4C,9G 2C,9G 0 Crabgrass      2C,9G 2C,7G 3C,7G 3G 0 1H 8G 4C,9G 2C,8G 2C,5G 5G 0 Barnyardgrass 3C,9H      4C,9H 6C,9H 4C,9H 0 2H 4C,9H 9C 9C 3C,8H 3C,9H 0 Cheatgrass 9G 6G 6C,9G      5C,9G 0 0 4C,9G 9C 6C,9G 2C,8G 9G 0 Wild Oats 3C,9G 3C,9G 5C,9G 5C,9G 0      0 6C,9G 9C 9C 3C,5G 3C,5G 0 Wheat 8G 9G 7G 8G 0 0 4C,9G 9C 9C 6G 9G 0      Corn 5C,9H 3C,9G 4U,9C 5C,9G 0 2H 4U,9G 7U,9C 7U,9C 3C,9H 9G 2C,7H      Soybean 5C,9G 4C,9G 9C 4C,9G 1H 3H 5C,9G 9C 9C 5C,9G 4C,9G 3C,8G Rice      5C,9G 6C,9G 5C,9G 5C,9G 2G 5G 9C 9C 9C 2C,9G 5C,9G 6G Sorghum 4C,9H      5C,9H 9C 4C,9G 0 5G 9C 9C 9C 3C,9H 9H 6G Sugar beet 9C 9C 9C 5C,8H 1H 3H      9C 9C 9C 9C 3C,8G 2H Cotton 9C 5C,9G 9C 4C,7H 0 0 9C 9C 2C,9G 4C,9G      3C,9G 2C,2G Giant Foxtail Barley PRE-EMERGENCE Morningglory 9G 9G 9G 8G      5G 2G 9G 9G 4C,9G 9G 8G 0 Cocklebur 8H 9H 9H 5G 0 0 10H 9H 3C,9H 8G 8H      8H Velvetleaf 9G 3G 9C -- 0 0 9C 9G 4C,9G 8G 4C,9G 3G Nutsedge 3C,8G 0      4C,8G 0 0 0 4C,9G 10E 10E 4G 5G 0 Crabgrass 0 0 2C,8G 7G 4G 2G 4C,8G      4C,9G 3C,7G 3G 4G 0 Barnyardgrass 4C,9H 5G 3C,8G 2H 0 0 4C,9G 4C,9H      5C,9H 3C,8H 9H 0 Cheatgrass 8G 5G 4C,9H 2C,5G 2G 0 4C,8H 4C,9G 4C,8H 8H      3C,9H 0 Wild Oats 3C,8G 3C,8G 4C,8G 3C,6G 0 0 3C,8G 5C,9G 5C,9G 3C,8G      3C,9G 0 Wheat 3C,9G 3C,9H 6G 5G 0 2G 5G 10E 5C,9G 7G 9G 0 Corn 3C,9G      2C,9H 3C,9G 4G 0 2G 8G 4C,9H 3C,9G 2C,7G 2C,9G 0 Soybean 8H 3C,5H 3C,5H      3G 2G 4H 2G 8H 2C,5H 3C,5H 4C,8H 2C,2H Rice 3C,9H 5C,9H 4C,8H 2C 0 2G 9H      10E 10E 2C,8G 8H 0 Sorghum 10E 9H 4C,9H 3C,5G 0 0 2C,9G 10E 5C,9H 3C,9H      10E 0 Sugar beet 7G 4C,7G 10C 4C,8H 0 0 10C 4C,9G 10C 9C 4C,9G 8G Cotton      8G 6G 2C,8G 8G -- -- 9C 9G 8G 9G 9G 3G Giant Foxtail Barley        Compound 13 Compound 14 Compound 15 Compound 16 Compound 17 Compound      18 Compound 19 Compound 20 Cmpd. 21 Cmpd. 22 Cmpd. 23 Cmpd. 24 Cmpd. 25      Cmpd. 26 Rate kg/ha 0.05 0.05 0.05 0.4 0.05 0.05 0.05 0.05 0.05 0.05      0.05 0.05 0.05 0.05 0.05        POST-EMERGENCE Morningglory 2C,4G 3C,9G 4C,8H 10C 1C,1H 3G 1H 3G 0 10C 1      0C 9C 9C 9C 10C Cocklebur 5G 5C,9G 9H 10C 3C,9H 5C,9H 6G 4C,9G 4C,9G 10C      9C 10C 9C 10C 10C Velvetleaf 0 2C,6H 4C,8H 9C 5C,9G 4C,9G 6H 2C,7G 2C,5G      10C 9C 9C 5C,9G 5C,9G 10C Nutsedge 2C,4G 0 0 5C,9G 4C,9G 3C,6G 0 0 5G      5C,9G 4C,9G 4C,9G 2C,8G 5C,9G 5C,9G Crabgrass 0 2G 4G 4C,9G 3G 3C,4G 0      4G 4G 0 0 2G 0 2G 0 Barnyardgrass 0 2C,3H 4C,8H 6C,9H 3C,9H 3C,9H 1C,2H      3C,7H 3C,8H 10C 4C,9H 9C 3C,8H 3C,8H 4C,9H Cheatgrass 0 0 2C,5G 2C,8G 2G      4G 0 0 0 5C,9G 3C,9G 9G 2G 7G 2C,9G Wild Oats 0 2G 3C,9G 3C,9G 4G 0 0 0      0 2C,5G 0 10C 0 3G 9C Wheat 0 3G 6G 5C,9G 5G 2G 0 0 0 4C,9G 7G 2C,9G 0      4G 4G Corn 0 3C,8H 4C,9H 4C,9G 2C,9H 3C,9H 3C,7H 3C,9H 4C,9G 9C 4C,9H 9C      2C,5G 9C 10C Soybean 3H 5C,9G 5C,9G 5C,9G 2C,7G 3C,7G 2H 2C,5H 3H,5G 9C      4C,9G 3C,9G 3H,4G 5C,9G 10C Rice 5G 2C,8G 5C,9G 5C,9G 4C,9G 2C,8G 5G      2C,9G 5C,9G 9C 4C,9G 9C 4C,9G 9C 9C Sorghum 2C,5G 3C,8H 3C,9H 3C,9H      5C,9G 4C,9H 2C,5G 3C,8G 4C,9H 9C 2C,9H 9C 9H 3C,9H 9C Sugar beet 3C,5G      4C,9G 9C 9C 3C,6G 4G 2G 3C,4H 3C,6H 9C 9C 9C 5C,9G 5C,9G 10C Cotton      3C,7G 2C,5G 4C,8G 9C 5C,9G 9C 4G 3C,5G 3C,5G 9C 5C,9G 10C 10C 10C 10C      Giant Foxtail          3C,6G 3C,6G 4C,9G 1H 3C,9G 4C,9G Barley      8G 9G 9C 2G 4G 7G PRE-EMERGENCE Morningglory 8G 7H 7G 9G 8G 9G 2H 8G 6G      9G 9H 7H 9G 8G 9G Cocklebur -- 9H 7H 8H 9H 8H 7H 8H 8G 9H 9H 9H 9H -- --      Velvetleaf 5G 4G 5H 5C,9G 9G 4C,9G 4G 7G 5G 10C 9C 8G 8G 6G 4C,9G      Nutsedge 5G 0 4G 7G 2C,7G 5G 0 0 0 9G 8G 9G 0 8G 10E Crabgrass 2G 0 0 5G      0 4G 0 0 0 0 2G 2G 0 4G 3G Barnyardgrass 0 1C 2C,5G 3C,9H 3C,9H 3C,9H 2C      5H 3C,7G 4C,9H 4C,9H 4C,8H 2C,5G 3C,6G 3C,8H Cheatgrass 0 2G 6G 3C,8H      3C,6G 3C,7G 0 0 0 3C,9H 9G 9G 4G 6G 9H Wild Oats 0 2C,4G 2C,8G 5C,9G      3C,8G 3C,8G 0 0 0 7G 3C,7G 7G 0 2G 2C,8G Wheat 0 6G 2C,9G 9C 7G 3C,9G 0      0 0 9H 9G 8G 0 4G 3C,9H Corn 5G 2C,6G 3C,9G 9G 9G 3C,9H 3C,6G 3C,9H 9G      3C,9H 9H 5C,9H 7G 3C,9G 3C,9G Soybean 2C,2G 6H 3C,6H 9H 3C,4G 3C,7H 1C      2C,4G 2C,6G 2C,7H 3C,8H 4C,6H 0 2C,6G 3C,7H Rice 2C 8G 2C,8H 10E 4C,8H      4C,8H 2C,5G 3C,9H 9H 4C,9H 2C,8G 4C,9H 3C,7G 8G 9H Sorghum 2C,4G 2C,7H      3C,9H 5C,9H 4C,9H 3C,9H 5G 3C,8H 3C,9H 4C,9H 9H 5C,9H 4C,8H 3C,8H 3C,9H      Sugar beet 6G 10C 4C,9G 9C 4C,8G 4C,9G 9G 3C,7G 4C,8G 5C,9G 9G 4C,9G 9G      5C,9G 5C,9G Cotton 6G 2G 7G 9G 7G 8G 5G 7G 7G 8G 9G 9G 8G 8G 9G Giant      Foxtail          3C,7G 3C,6G 4C,8G 2C,2G 2C,5G 3C,5G Barley          9G      9G 9G 7G 8G 9G         Cmpd. 27 Cmpd. 28 Cmpd. 29 Cmpd. 30 Cmpd. 31 Cmpd. 32 Cmpd. 33 Cmpd.      34 Cmpd. 35 Cmpd. 36 Cmpd. 37 Cmpd. 38 Cmpd. 39 Cmpd. 40 Cmpd. 41 Cmpd.      42 Cmpd. 43 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05      0.05 0.05 0.05 0.05 0.05 0.05 0.05        POSTEMERGENCE Morningglory 3C,7H 10C 9C 0 3G 10C 10C 10C 10C 10C 5C,9G 3      C,8G 10C 10C 10C 10C 10C Cocklebur 0 8H 9H 4C,9H 4C,9H 10C 9C 10C 10C 9C      4C,9H 4C,9G 10C 10C 10C 10C 10C Velvetleaf 0 10C 10C 8G 0 2C,5G 4C,8G      10C 10C 9C 5C,9G 4C,9H 10C 10C 9C 6G 3C,8G Nutsedge 0 6C,9G 4C,8G 0 0 5G      2C,5G 5C,9G 10C 4C,9G 5G 2G 9C 10C 9C 9C 2C,8G Crabgrass 0 0 0 0 0 0 2G      8G 9C 0 0 0 9C 5C,9G 4C,8G 3C,7G 2G Barnyardgrass 5H 4C,9H 3C,8H 0 4H      3C,9H 4C,9H 9C 9C 4C,9H 3C,8H 2C,5H 9C 9C 9C 9C 9C Cheatgrass 0 7G 2C,5G      0 0 0 5G 4C,9G 9C 8G 8G 0 9C 9C 4C,9G 2C,9G 1C,5G Wild Oats 0 0 2C 0 0      2C,5G 3G 4C,8G 4C,9G 0 2G 0 9C 9C 5C,9G 9G 0 Wheat 0 0 0 0 0 0 3G 9G 9G      3G 3G 0 9C 2C,9G 9C 2C,9G 0 Corn 5H 3C,8H 9H 0 0 3C,9H 3C,9H 5C,9G 6C,9G      2H 0 3C,9H 9C 5C,9G 5C,9G 10C 4C,9G Soybean 3H 4C,9G 3H,9G 7G 2G 4C,9G      4C,9G 6C,9G 5C,9G 3C,9G 4C,9G 2C,7H 9C 9C 9C 9C 2C,8H Rice 0 3C,9G 8G 5G      0 4C,9G 5C,9G 9C 9C 5C,9G 4C,8G 3C,8G 9C 9C 9C 9C 4C,9G Sorghum 3G 7G      3C,9H 3C,7H 2G 2C,7G 4C,9H 9C 9C 4C,9H 2C,7G 3C,8H 9C 9C 9C 3C,9G 3C,9G      Sugar beet 4C,6G 10C 10C 6C,9G 2G 10C 9C 9C 10C 9C 3C,7H 5C,9G 9C 9C 9C      9C 2C,4G Cotton 0 4C,9G 4C,9G 5G 4C,8G 9C 4C,9G 10C 10C 4C,9G 4C,9H      4C,8H 10C 10C 10C 9C 9C Giant Foxtail 0 3C,7G 4G 0 0 2C,4G 6G 5C,9G 9C      4G 2G 2G 10C 9C 9C 3C,8G 1C,6G Barley 0 2C 5G 0 0 2G 0 9C 5C,9G 9G 4C,9G      0 9C 9C 4C,9G 9C 6G PREEMERGENCE Morningglory 5G 7G 7G 5G 7G 8G 7G 10C      8G 1H 3G 7H 10E 9H 9G 9G 7G Cocklebur 8G 9H 8H 9H 9H 9H -- 9H 8H 3H 9H      7H 9H 9C 9H 8H 9H Velvetleaf 8G 9G 9G 9G 9G 9C 6G 9G 8G 5G 7H 7G 10E 9C      10C 8G 2C,4G Nutsedge 0 3G 10E 5G 10E 0 10E 8G 9G 3G 0 0 10E 10C 10E 10E      9G Crabgrass 0 5G 3G 0 0 0 0 0 3G 0 0 0 5C,9G 5C,9G 3G 2C,5G 9G Barnyardg      rass 0 4C,7H 4C,8H 2G 2G 3C,7G 2C,7G 4C,9H 3C,9H 7G 7H 2C 5C,9H 5C,9H      3C,9H 8H 9H Cheatgrass 0 5G 3C,7G 0 0 4G 0 9H 9H 3G 6G 0 10E 10E 8G 7G      4G Wild Oats 0 2G 5G 4G 0 5G 2G 2C,8G 3C,8G 0 2G 0 6C,9H 5C,9H 6C,9H      4C,9G 5G Wheat 0 0 5G 0 0 0 0 6C,9H 10H 0 3G 0 10E 10E 4C,9H 4C,9H 4G      Corn 2C,3G 7G 3C,8H 3G 2C,6G 2C,7G 2C,5G 9H 5C,9H 3C,7G 2C,6G 6G 10E      5C,9H 9H 4C,9H 2C,9H Soybean 0 2C,5H 3C,8H 1C 0 3C,5H 3C,3H 7H 3C,7G 2H      2C,5G 2C 9H 9H 9H 4C,8H 2C,7H Rice 4G 2C,6H 4C,9H 3G 3G 9H 7G 10E 10E 8H      3C,7H 2C,5G 10H 10E 10E 10E 4C,9H Sorghum 0 2C,4H 3C,5G 5G 5G 5G 3C,3H      5C,9H 10H 3C,7G 4C,9H 2C,5G 10H 10E 10H 5C,9H 2C,9H Sugar beet 8G 10C 9C      8G 9G 10C 8G 9G 8G 7H 5H 5G 9C 5C,9G 5C,9G 4C,9G 2C,4G Cotton 3G 7G 7G      7G 8G 7G 6G 9G 9G 2G 0 6G 9C 10C 9G 9G 9G Giant Foxtail 0 4C,6G 4C,7G 5G      4G 8G 0 4C,9H 3C,8G 2G 3G 1C 9C 5C,9H 3C,9H 3C,8G 2C,4G Barley 2G 7G 9G      3G 0 2C,8G 2G 9G 9G 9G 3C,9G 3G 4C,9G 5C,9H 3C,9H 4C,9H 7G         Cmpd. 44 Cmpd. 45 Cmpd. 46 Cmpd. 47 Cmpd. 48 Cmpd. 49 Cmpd. 50 Cmpd.      51 Cmpd. 52 Cmpd. 53 Cmpd. 54 Cmpd. 55 Cmpd. 56 Cmpd. 57 Cmpd. 58 Cmpd.      59 Cmpd. 60 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05      0.05 0.05 0.05 0.05 0.05 0.05 0.05        POSTEMERGENCE Morningglory 5C,9H 5C,9G 5C,8H 10C 10C 10C 9C 9C 6G      3C,8H 10C 10C 6C,9G 10C 2C,7G 10C 10C Cocklebur 2C,8H 2C,6G 4C,9H 10C      10C 9C 4C,9G 9C 4C,9H 3C,8H 10C 9H 2C,9H 10C 10C 10C 10C Velvetleaf      2H,5G 0 2G 5C,9G 3C,8G 10C 3C,6G 3C,5H 2H 2C,3H 10C 9C 10C 9C 9C 9C 10C      Nutsedge 2C,8G 0 0 4C,9G 2C,9G 4G 4G 5G 4G 0 3C,9G 2C,9G 2C,7G 4C,9G 9G      9G 4C,9G Crabgrass 0 2G 1C,3G 2C,4G 7G 2C,7G 4G 4G 3G 8G 0 3G 3G 0 3G 5G      4G Barnyardgrass 4C,9H 8H 9C 9C 9C 9C 9C 9C 9C 5C,9H 4C,9G 4C,8G 1C,7G      2C,6G 2C,6H 5C,9H 5C,9H Cheatgrass 3G 2G 2C 2C,5G 4C,9G 6G 4G 5G 0 7G      3C,9G 3C,9G 8G 6G 2C,6G 2C,7G 9G Wild Oats 0 0 0 2C,6G 3C,9G 2C,4G 0 0 0      0 3G 2C,5G 2C,6G 1C 0 0 3C,5G Wheat 0 0 0 6G 4C,9G 3G 3G 2G 0 3G 8G 9G      7G 2G 0 2G 6G Corn 3C,9G 2C,4H 9G 4U,9G 4U,9G 4C,9H 2C,8G 3C,9G 2C,9H      2C,9H 9G 2C,9G 3C,9H 5G 3C,7G 3C,7H 2U,9G Soybean 2C,7H 1C,1H 2H 9C 9C      9C 5C,9G 5C,9G 3C,7H 8G 3C,9G 3C,9H 2C,8G 0 4C,9G 5C,9G 9C Rice 3C,9G 2G      5C,9G 5C,9G 6C,9G 9C 9C 9C 9C 9C 2C,9G 9G 2C,9G 5G 7G 9G 4C,9G Sorghum      3C,9G 8G 2C,8H 9C 6C,9G 9C 3C,8G 9H 4C,9G 4C,9G 9G 2C,9G 2C,9G 3C,9G      3C,8H 3C,9G 4C,9G Sugar beet 2C,6G 0 3C,7H 10C 9C 10C 5C,9G 2C,6G 3C,5H      8G 9C 9C 9C 5C,9G 4C,9G 9C 9C Cotton 3C,8G 3C,8G 2C,6G 10C 9C 10C 10C      10C 10C 3C,5G 9C 9C 10C 10C 10C 9C 10C Giant Foxatil 0 0 2C,5G 5C,9H      4C,9G 9C 3C,7H 4C,9G 6G 3C,9G 5G 2C,9G 7G 5G 5G 7G 3C,6G Barley 2C,9G 0      0 3C,8H 4C,9G 4C,9G 3C,7G 2C,7G 6G 2C,5G 9G 8G 8G 4G 3G 5G 9G PREEMERGENC      E Morningglory 4G 2C,5G 0 9G 8G 8H 1H 7H 0 0 0 7G 3H 3G 6H 6G 5G      Cocklebur 2C,7G 2C,5H 0 9H 8H 9H 0 2C,2H 1H 0 3H -- 2C,3H 8H 2C,2H 5H 7H      Velvetleaf 4G 0 0 3C,7G 8G 4G 2G 2G 0 0 1C,5G 4C,7G 2C,7G 5G 6G 7G 7G      Nutsedge 7G 3C,8G 0 5G 3C,9G 7G 0 4G 8G 0 7G 3C,9G 7G 0 10E 7G 5G      Crabgrass 2C,8G 0 0 0 3G -- 5G 8G 8G 0 2G 0 0 2G 3G 5G 2G Barnyardgrass      2C,7H 3C,8H 2C,8H 9H 3C,9H 9H 3C,9H 4G 9H 0 3C,7H 2C,9H 2C,9H 7G 5G      3C,8H 9H Cheatgrass 2G 0 0 8G 8G 2C,7G 7G 0 0 0 5G 7H 7H 3G 3G 5G 8G      Wild Oats 2G 0 0 6G 8G 8G 4G 6G 4G 0 2G 2C,3G 2C,5G 0 2G 2G 2G Wheat 0 0      0 7G 9H 5G 6G 7G 4G 0 0 7G 5G 0 2G 3G 7G Corn 5C,9H 2C,8H 0 3C,9G 3C,9G      3C,9G 2C,7G 2C,6G 2C,3G 0 2G 6G 1C,6G 2G 3G 2C,6G 3C,8H Soybean 2C,5H 0      0 7H 3C,7H 3C,9H 3C,8H 3C,8H 2C,3H 0 3C 3C,7H 2C,7H 0 2C,5G 3C,4H 7H      Rice 5C,9H 2C,8H 0 3C,9H 9H 5C,9H 9H 9H 5C,9H 5G 3C,7H 3C,7G 3C,8H 5G      4C,8H 5C,9H 8H Sorghum 3C,9H 2C,9H 0 9H 9H 9H 9H 9H 9H 4G 2C,7H 2C,9H      3C,9H 3C,6G 3C,5G 4C,8G 3C,9H Sugar beet 2C,4G 0 0 3C,9G 9G 9G 4H 7G 3G      0 4C,8G 4C 3C 8G 9G 9G 6H Cotton 2C,6G 1C,3G 0 8G 9G 9G 8G 3C,9G 8G 0 0      2C,4G 3G 0 3G 2G 0 Giant Foxtail 2C,5G 0 0 3C,7G 8G 6G 3G 4G 0 0 2G 7G      2G 2G 5G 6G 0 Barley 6G 7G 0 7G 9G 2C,9G 2G 4G 2C,5G 0 5G 8G 4G 0 5G 5G      2C,8G         Cmpd. 61 Cmpd. 62 Cmpd. 63 Cmpd. 64  Cmpd. 65 Cmpd. 68 Cmpd. 67 Cmpd.      68 Cmpd. 69 Cmpd. 70 Cmpd. 71 Cmpd. 72 Cmpd. 73 Cmpd. 74 Cmpd. 75 Cmpd.      76 Cmpd. 77 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05      0.05 0.05 0.05 0.05 0.05 0.05 0.05        POSTEMERGENCE Morningglory 10C 10C 10C 10C 10C 2C,5G 2C,6G 2H 1H 2C,4G 4      C,9H 10C 10C 9C 10C 10C 10C Cocklebur 10C 10C 10C 10C 10C 3C,9H 2C,6G 2H      2C,7H 5H 3C,9H 10C 10C 10C 10C 10C 10C Velvetleaf 10C 9C 3C,8G 3C,9G 9C      2C,9G 2C,5H 1H 5H 2C,5G 9C 10C 10C 10C 10C 10C 10C Nutsedge 4C,9G 3C,9G      3G 2C,8G 2C,8G 3C,9G 2C,5G 4G 0 0 2C,8G 5C,9G 9C 9C 6C,9G 2C,8G 9G      Crabgrass 3G 5G 2G 0 0 5G 0 0 0 0 5G 7G 0 3C,8H 0 3G 6G Barnyardgrass 9C      9C 4C,9H 3C,8G 3C,9G 3C,9H 9H 7H 0 6H 2C,7G 9C 9C 9C 9C 9H 9C Cheatgrass      4C,9G 3C,9G 2C,4G 2C,5G 8G 4G 6G 0 2G 0 0 9C 9C 9C 3C,9G 9C 5C,9G Wild      Oats 2C,7G 5C,9G 2G 2C,7G 2C,9G 5G 2C,7G 0 2G 2C,3G 2C,8G 3C,8G 5C,9G 9C      2C,5G 9C 9C Wheat 3C,9G 3C,9G 4G 2G 3G 2G 5G 0 4G 0 6G 2C,9G 9G 9G 3G      4C,9G 4C,9G Corn 9C 2U,9G 3C,7H 2C,7G 3C,9H 3C,9H 2C,9H 0 2C,5G 3C,9H      3C,9H 4U,9G 2U,9G 9G 3C,9H 2C,8H 3U,9G Soybean 9C 9C 3C,3H 4C,9G 5C,9G      5H 3C,7H 1H 3C,7H 2C,3H 4C,9H 9C 9C 9C 5C,9G 9C 9C Rice 5C,9G 5C,9G 9G      2C,8G 5C,9G 2C,7G 3C,7G 2G 3C,9G 8G 2C,6G 9C 9C 9C 5C,9G 9C 9C Sorghum      5C,9G 4C,9G 4C,9G 3C,9H 9G 3C,6G 3C,8H 5G 3C,9H 3C,9H 2C,9H 9C 5C,9G 9C      9C 4C,9G 5C,9G Sugar beet 9C 9C 4C,8H 9C 9C 2C,7G 3C,8H 3G 3C,6G 3C,7H      2C,6G 10C 10C 10C 9C 10C 9C Cotton 10C 10C 4C,9G 3C,8G 9C 7G 3C,8G 0 4G      2C 2C,8G 10C 10C 9C 10C 4C,9G 10C Giant Foxtail 3C,8G 3C,8G 4G 4G 2C,7G      2C,6G 2C,6G 2G 2G 2G 6G 9C 6C,9G 6C,9H 5C,9G 4C,9G 4C,9G Barley 9H 9H      3C,6G 4G 2C,6G 8G 7G 0 3G 0 3C,8G 3C,9G 4C,9G 4C,9G 4C,9H 4C,9G 3C,9G      PREEMERGENCE Morningglory 4C,8G 5H 8G  2C,8G 2C,8G 0 0 0 3G 0 2G 9G 9G      9G 8G 9G 9G Cocklebur 7H 6H 2C,4H 3C,7H 6H 2H 0 -- -- 0 5H 6H -- 9H      3C,5H 9H 9H Velvetleaf 7H 3C,8H 7G 5G 4G 0 0 0 3G 0 0 2C,8G 9C 5C,9G 5H      4C,8H 4C,8H Nutsedge 8G 8G 5G 8G 2C,8G 0 0 0 0 3G 0 9G 10E 10E 9G 5G 4G      Crabgrass 3G 0 0 0 0 0 5G 0 0 3G 7H 0 3G 2G 0 0 0 Barnyardgrass 9H 7G 8H      7H 7H 0 7G 9H 0 3G 2C,6H 8H 9H 9H 9H 8H 8H Cheatgrass 5C,9G 8G 5G 2G 6H      0 2G 0 0 3G 2C,6H 8G 9H 9H 9H 9H 9H Wild Oats 4C,8G 3C,8H 2G 2C,3G 3C,8G      0 2G 0 0 4G 0 8G 3C,9G 2C,9H 3C,6G 3C,9G 4C,9G Wheat 4C,9H 9G 3G 0 0 0      2G 0 0 0 2G 8G 3C,9G 3C,9H 5G 9H 4C,9H Corn 3C,9H 3C,9H 3C,4G 2C,5G      3C,6G 2G 2C,7G 2G 0 3G 2C,6H 9G 3C,9H 3C,9G 3C,9H 7G 2C,9G Soybean 4C,7H      7G 0 3C,7H 4C,8H 0 1H 0 0 0 0 7H 9H 9H 7H 3C,8H 9H Rice 5C,9H 9H 7H 9H      10H 4G 3G 4G 0 5G 3C,7G 3C,9H 9H 10E 9H 10E 10E Sorghum 9H 9H 9H 3C,8H      9H 5G 3C,7G 4G 0 6G 2C,9H 9G 9H 10E 3C,9H 9H 10H Sugar beet 9C 3C,7G 8G      3C,8G 3C,9G 3G 8G 0 2G 5G 6G 7G 4C,9G 9G 8G 4C,8G 9G Cotton 3C,8H 2C,7G      9G 2C,5G 2C,8G 0 2G 0 4G 5G 0 7G 9G 9G 9G 9G 9G Giant Foxtail 6G 5G 4G 0      0 0 5G 0 10H -- 5H 5G 3C,9H 7G 3C,6G 5G 5G Barley 9G 8G 0 0 2G 0 7G 4G      3G 4G 0 8G 9G 9G 7G 9G 9G 

What is claimed is:
 1. A compound of the formula: ##STR56## wherein E is CH₂ or a single bond;W is O or S; R is H or CH₃ ; R₁ is F, Cl, Br, NO₂, C₁ -C₄ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, OCH₂ CH₂ OCH₃, C₁ -C₄ haloalkoxy, C₃ -C₄ alkenyloxy, C₂ -C₄ haloalkenyloxy, C₃ -C₄ alkynyloxy, CO₂ R₃, CONR₄ R₅, SO₂ NR₄ R₅, SO₂ N(OCH₃)CH₃, S(O)_(n) R₆, OSO₂ R₇, C₁ -C₂ alkyl substituted with C₁ -C₂ alkoxy, OH or C₁ -C₂ alkylthio, ##STR57## R₂ is ##STR58## R₃ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, ##STR59## CH₂ CH₂ Cl, CH₂ CH₂ F, or C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ ; R₄ is C₁ -C₃ alkyl; R₅ is H or C₁ -C₃ alkyl; R₄ and R₅ may be taken together to form (CH₂)₃ or (CH₂)₄ ; R₆ is C₁ -C₃ alkyl, CH₂ CH═CH₂ or CH₂ C.tbd.CH; R₇ is C₁ -C₃ alkyl or N(CH₃)₂ ; R₈ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CH₂ CH₂ Cl, CH₂ CH₂ F, C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ and C₃ -C₆ cycloalkyl; R₉ is C₁ -C₂ alkyl; R₁₀ and R₁₁ are independently C₁ -C₂ alkyl, C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, NHCH₃ or N(CH₃)₂ ; R₁₂ and R₁₃ are independently H or C₁ -C₂ alkyl; R₁₄ is C₁ -C₃ alkyl; R₁₅ is H or CH₃ ; R₁₆ is H, C₁ -C₂ alkyl or F; R₁₇ is H or C₁ -C₂ alkyl; R₁₈ is C₁ -C₂ alkyl; R₁₉ is H, Si(CH₃)₃ or C₁ -C₂ alkyl; R₂₀ is H or C₁ -C₂ alkyl; p is 1 or 2; n is 0, 1, or 2; A is ##STR60## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, halogen, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino or di(C₁ -C₃ alkyl)amino; Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylthioalkyl, C₂ -C₅ alkylsulfinylalkyl, C₂ -C₅ alkylsulfonylalkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkynyl, C₃ -C₅ cycloalkyl, azido, cyano, ##STR61## m is 2 or 3; Q₁ and Q₂ are independently O or S; R_(a) is H or C₁ -C₃ alkyl; R_(b) and R_(c) are independently C₁ -C₃ alkyl; Z is CH, CCH₃, CC₂ H₅, CCl or CBr;and their agriculturally suitable salts; provided that (1) when X is halogen, then Z is CH and Y is OCH₃, OC₂ H₅, NH₂, NHCH₃, N(CH₃)₂, OCF₂ H or N(OCH₃)CH₃ ; (2) when X or Y is C₁ haloalkoxy, then Z is CH; (3) when W is S, then R is H, Z is CH and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, ##STR62## (4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R₁ and R₂ is less than or equal to six; (5) when R₂ is C(O)R₁₇, then R₁ is other than C₁ -C₄ haloalkyl or C₂ alkyl substituted with C₁ -C₂ alkoxy or C₁ -C₂ alkylthio, and Y is other than cyclopropyl; (6) when Y is C₂ -C₅ alkylthioalkyl, C₂ -C₅ alkylsulfinylalkyl or C₂ -C₅ alkylsulfonylalkyl, then R₂ is other than CH(R₁₇)NO₂.
 2. A compound of claim 1 whereW is O; and R is H.
 3. A compound of claim 2 whereE is a single bond; X is C₁ -C₂ alkyl, C₁ -C₂ alkoxy, Cl, F, Br, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; and Y is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, CH₂ OCH₃, CH₂ OCH₂ CH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, CH₂ SCH₃, ##STR63## OCF₂ H, SCF₂ H, cyclopropyl, C.tbd.CH or C.tbd.CCH₃ ; Z is CH.
 4. A compound of claim 3 where R₂ is CH₂ CN, CH₂ N₃, ##STR64##
 5. A compound of claim 4 where R₁ is F, Cl, Br, NO₂, C₁ -C₃ alkyl, C₁ -C₂ alkyl subsituted with 1-3F of Cl or 1Br, C₂ -C₃ alkenyl, C₂ -C₃ alkenyl substituted with 1-3F or Cl, C₁ -C₂ alkoxy, C₁ -C₂ alkoxy subsituted with 1-3F or Cl or 1-Br, allyloxy, propargyloxy, OC(Cl)═CHCl, CO₂ CH₃, CO₂ C₂ H₅, CO₂ CH₂ CH═CH₂, CO₂ CH₂ CH₂ Cl, CO₂ CH₂ CH₂ OCH₃, CONH(C₁ -C₂ alkyl), CONCH₃ (C₁ -C₂ alkyl, SO₂ N(OCH₃)CH₃, SO₂ NH(C₁ -C₂ alkyl), SO₂ N(C₁ -C₂ alkyl)₂, S(O)_(n) C₁ -C₃ alkyl, OSO₂ C₁ -C₃ alkyl, C₁ -C₂ alkyl substituted with OCH₃ or SCH₃, C₆ H₅ and R₁ -A, R₁ -B, R₁ -C, R₁ -D, R₁ -E, R₁ -F, R₁ -G, R₁ -H, R₁ -I,R₁ -J, R₁ -K, R₁ -L, R₁ -M, R₁ -N, R₁ -O, R₁ -P, R₁ -Q R₁ -R, R₁ -S, R₁ -T, R₁ -U, R₁ -V or R₁ -W.
 6. A compound of claim 5 whereX is CH₃, OCH₃, OCH₂ CH₃, Cl, OCF₂ H or OCH₂ CF₃ ; and Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.
 7. A compound of claim 6 where R₁ is F, Cl, Br, NO₂, CH₃, CF₃ C₁ -C₂ alkoxy, allyloxy, OC(Cl)═CHCl, CO₂ CH₃, CO₂ C₂ H₅, CO₂ NHCH₃, CO₂ N(CH₃)₂, SO₂ NHCH₃ SO₂ N(CH₃)₂, SO₂ CH₃, SO₂ C₂ H₅, OSO₂ CH₃, OSO₂ C₂ H₅, R₁ -A, R₁ -B or R₁ -C.
 8. The compound of claim 1 which is 4-(cyanomethyl)-2-[[4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.
 9. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 10. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 11. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 14. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
 15. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
 16. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
 17. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 18. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 5. 22. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 6. 23. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 7. 24. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim
 8. 